EA039880B1 - Способ получения оптически активного соединения - Google Patents

Info

Publication number

EA039880B1

EA039880B1 EA201992709A EA201992709A EA039880B1 EA 039880 B1 EA039880 B1 EA 039880B1 EA 201992709 A EA201992709 A EA 201992709A EA 201992709 A EA201992709 A EA 201992709A EA 039880 B1 EA039880 B1 EA 039880B1

Authority

EA

Eurasian Patent Office

Prior art keywords

group

acid

compound

salt

reaction

Prior art date

2017-05-30

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 365
• 238000004519 manufacturing process Methods 0.000 title claims description 32
• 150000003839 salts Chemical class 0.000 claims abstract description 242
• 238000000034 method Methods 0.000 claims abstract description 100
• 238000006722 reduction reaction Methods 0.000 claims abstract description 27
• -1 thiocarbamoyl group Chemical group 0.000 claims description 293
• 125000001424 substituent group Chemical group 0.000 claims description 106
• 239000003446 ligand Substances 0.000 claims description 92
• 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 87
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 78
• 125000003118 aryl group Chemical group 0.000 claims description 61
• 229910052723 transition metal Inorganic materials 0.000 claims description 48
• 150000003624 transition metals Chemical class 0.000 claims description 45
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 43
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 40
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 39
• 125000005843 halogen group Chemical group 0.000 claims description 36
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 34
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 33
• 229910052741 iridium Inorganic materials 0.000 claims description 33
• GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical group [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 33
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 29
• 125000003277 amino group Chemical group 0.000 claims description 28
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
• 125000000217 alkyl group Chemical group 0.000 claims description 25
• 229910052799 carbon Inorganic materials 0.000 claims description 25
• 125000000623 heterocyclic group Chemical group 0.000 claims description 24
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 23
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 22
• 229910052717 sulfur Inorganic materials 0.000 claims description 21
• VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 claims description 19
• 125000004432 carbon atom Chemical group C* 0.000 claims description 18
• 239000000460 chlorine Substances 0.000 claims description 17
• 229910001914 chlorine tetroxide Inorganic materials 0.000 claims description 16
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
• VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 16
• 125000003545 alkoxy group Chemical group 0.000 claims description 15
• 229960002510 mandelic acid Drugs 0.000 claims description 15
• QCHAVHXSBZARBO-UHFFFAOYSA-N (r)-monophos Chemical compound C1=CC2=CC=CC=C2C2=C1OP(N(C)C)OC1=C2C2=CC=CC=C2C=C1 QCHAVHXSBZARBO-UHFFFAOYSA-N 0.000 claims description 14
• QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims description 13
• IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims description 13
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 12
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 12
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 11
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
• 238000010537 deprotonation reaction Methods 0.000 claims description 11
• 125000006239 protecting group Chemical group 0.000 claims description 11
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 10
• 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 10
• 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 9
• 238000009876 asymmetric hydrogenation reaction Methods 0.000 claims description 8
• 239000003638 chemical reducing agent Substances 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 7
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
• 125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 claims description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 5
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 5
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
• 125000005842 heteroatom Chemical group 0.000 claims description 5
• 229910052760 oxygen Chemical group 0.000 claims description 5
• 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 claims description 4
• NXLACVVNHYIYJN-UHFFFAOYSA-N 1-phenyl-n-(1-phenylethyl)ethanamine Chemical compound C=1C=CC=CC=1C(C)NC(C)C1=CC=CC=C1 NXLACVVNHYIYJN-UHFFFAOYSA-N 0.000 claims description 4
• 229910020366 ClO 4 Inorganic materials 0.000 claims description 4
• RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 claims description 4
• 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 4
• 125000000213 sulfino group Chemical group [H]OS(*)=O 0.000 claims description 4
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
• 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
• 125000004043 oxo group Chemical group O=* 0.000 claims description 3
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
• 229910052736 halogen Inorganic materials 0.000 claims description 2
• 150000002367 halogens Chemical class 0.000 claims description 2
• 239000001301 oxygen Chemical group 0.000 claims description 2
• 239000011593 sulfur Chemical group 0.000 claims description 2
• FUXJMHXHGDAHPD-UHFFFAOYSA-N pyrimidine-2-carboxamide Chemical class NC(=O)C1=NC=CC=N1 FUXJMHXHGDAHPD-UHFFFAOYSA-N 0.000 abstract description 8
• 238000010511 deprotection reaction Methods 0.000 abstract 1
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 239
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 214
• 239000002904 solvent Substances 0.000 description 166
• 238000006243 chemical reaction Methods 0.000 description 150
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 116
• 238000004128 high performance liquid chromatography Methods 0.000 description 104
• 239000000203 mixture Substances 0.000 description 101
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 98
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 66
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 65
• 239000010948 rhodium Substances 0.000 description 64
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 61
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 53
• 239000000758 substrate Substances 0.000 description 53
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 50
• 230000002829 reductive effect Effects 0.000 description 50
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
• 229910001868 water Inorganic materials 0.000 description 46
• 238000005481 NMR spectroscopy Methods 0.000 description 43
• 239000007787 solid Substances 0.000 description 42
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 39
• 239000002253 acid Substances 0.000 description 39
• 238000003786 synthesis reaction Methods 0.000 description 39
• 230000014759 maintenance of location Effects 0.000 description 37
• 238000000825 ultraviolet detection Methods 0.000 description 37
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 36
• 239000000654 additive Substances 0.000 description 36
• 230000000996 additive effect Effects 0.000 description 35
• 230000015572 biosynthetic process Effects 0.000 description 33
• 230000003287 optical effect Effects 0.000 description 33
• 239000000243 solution Substances 0.000 description 33
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 31
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 31
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
• 239000007864 aqueous solution Substances 0.000 description 30
• 229910052739 hydrogen Inorganic materials 0.000 description 30
• 239000001257 hydrogen Substances 0.000 description 29
• 235000001014 amino acid Nutrition 0.000 description 28
• 238000010606 normalization Methods 0.000 description 28
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 28
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
• 239000003054 catalyst Substances 0.000 description 27
• 238000001914 filtration Methods 0.000 description 27
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 26
• 238000004458 analytical method Methods 0.000 description 26
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 26
• 239000002585 base Substances 0.000 description 25
• 239000007858 starting material Substances 0.000 description 25
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 24
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
• BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 24
• 229910000402 monopotassium phosphate Inorganic materials 0.000 description 24
• 235000019796 monopotassium phosphate Nutrition 0.000 description 24
• PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 24
• 239000000126 substance Substances 0.000 description 24
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 23
• 230000002378 acidificating effect Effects 0.000 description 22
• 150000001413 amino acids Chemical class 0.000 description 22
• 238000006268 reductive amination reaction Methods 0.000 description 22
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• 235000011054 acetic acid Nutrition 0.000 description 21
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 21
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 20
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 20
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 20
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 20
• 125000004429 atom Chemical group 0.000 description 20
• MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 20
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 20
• RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 20
• USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 20
• UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 20
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 20
• HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 20
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 20
• AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 20
• 230000000052 comparative effect Effects 0.000 description 19
• 229910052751 metal Inorganic materials 0.000 description 19
• 239000002184 metal Substances 0.000 description 19
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
• SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 18
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 18
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
• 229910052786 argon Inorganic materials 0.000 description 18
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 17
• 150000001721 carbon Chemical group 0.000 description 17
• 238000002425 crystallisation Methods 0.000 description 17
• 230000008025 crystallization Effects 0.000 description 17
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 16
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 16
• AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 16
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 16
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 16
• DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 16
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 description 16
• PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 16
• ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 16
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 16
• YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 16
• ASNHGEVAWNWCRQ-UHFFFAOYSA-N 4-(hydroxymethyl)oxolane-2,3,4-triol Chemical compound OCC1(O)COC(O)C1O ASNHGEVAWNWCRQ-UHFFFAOYSA-N 0.000 description 15
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 15
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 15
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
• 125000004122 cyclic group Chemical group 0.000 description 15
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 15
• 238000005984 hydrogenation reaction Methods 0.000 description 15
• 150000002825 nitriles Chemical class 0.000 description 15
• 239000011541 reaction mixture Substances 0.000 description 15
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 15
• VUTUHLLWFPRWMT-QMDOQEJBSA-M (1z,5z)-cycloocta-1,5-diene;rhodium;trifluoromethanesulfonate Chemical compound [Rh].C\1C\C=C/CC\C=C/1.C\1C\C=C/CC\C=C/1.[O-]S(=O)(=O)C(F)(F)F VUTUHLLWFPRWMT-QMDOQEJBSA-M 0.000 description 14
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 14
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
• 239000012298 atmosphere Substances 0.000 description 14
• 150000002170 ethers Chemical class 0.000 description 14
• 150000002430 hydrocarbons Chemical group 0.000 description 14
• 150000002503 iridium Chemical class 0.000 description 14
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 13
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 13
• 239000003795 chemical substances by application Substances 0.000 description 13
• 235000019253 formic acid Nutrition 0.000 description 13
• 150000007529 inorganic bases Chemical class 0.000 description 13
• 150000007530 organic bases Chemical class 0.000 description 13
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 12
• KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 12
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 12
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 12
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 12
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
• 125000001309 chloro group Chemical group Cl* 0.000 description 12
• PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 12
• 150000008282 halocarbons Chemical class 0.000 description 12
• XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 12
• 150000003283 rhodium Chemical class 0.000 description 12
• 238000012360 testing method Methods 0.000 description 12
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 12
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 12
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
• VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 11
• 229910052783 alkali metal Inorganic materials 0.000 description 11
• 239000012299 nitrogen atmosphere Substances 0.000 description 11
• 125000002524 organometallic group Chemical group 0.000 description 11
• GYZZZILPVUYAFJ-UHFFFAOYSA-N phanephos Chemical compound C1CC(C(=C2)P(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=C2CCC2=CC=C1C=C2P(C=1C=CC=CC=1)C1=CC=CC=C1 GYZZZILPVUYAFJ-UHFFFAOYSA-N 0.000 description 11
• FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 11
• 238000002360 preparation method Methods 0.000 description 11
• 230000035484 reaction time Effects 0.000 description 11
• 150000003462 sulfoxides Chemical class 0.000 description 11
• 239000011975 tartaric acid Substances 0.000 description 11
• IWYDHOAUDWTVEP-ZETCQYMHSA-N (S)-mandelic acid Chemical compound OC(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-N 0.000 description 10
• MBNMGGKBGCIEGF-UHFFFAOYSA-N 1,1-diethoxypropane Chemical compound CCOC(CC)OCC MBNMGGKBGCIEGF-UHFFFAOYSA-N 0.000 description 10
• HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 10
• JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 10
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
• NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 10
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 10
• JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 10
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
• 150000001298 alcohols Chemical class 0.000 description 10
• 238000006482 condensation reaction Methods 0.000 description 10
• NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 10
• JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 10
• 235000019439 ethyl acetate Nutrition 0.000 description 10
• 239000012634 fragment Substances 0.000 description 10
• UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 10
• GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 10
• LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 10
• 239000007800 oxidant agent Substances 0.000 description 10
• 150000002940 palladium Chemical class 0.000 description 10
• 239000003208 petroleum Substances 0.000 description 10
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 10
• 150000003303 ruthenium Chemical class 0.000 description 10
• 229930195734 saturated hydrocarbon Natural products 0.000 description 10
• HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 10
• 150000003457 sulfones Chemical class 0.000 description 10
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 10
• 239000008096 xylene Substances 0.000 description 10
• 239000004912 1,5-cyclooctadiene Substances 0.000 description 9
• QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 9
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 9
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 9
• 125000002252 acyl group Chemical group 0.000 description 9
• 150000001408 amides Chemical class 0.000 description 9
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
• 229910052801 chlorine Inorganic materials 0.000 description 9
• 238000004587 chromatography analysis Methods 0.000 description 9
• 239000000706 filtrate Substances 0.000 description 9
• 238000010575 fractional recrystallization Methods 0.000 description 9
• 150000002576 ketones Chemical class 0.000 description 9
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
• 238000001953 recrystallisation Methods 0.000 description 9
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 9
• CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 8
• 238000005160 1H NMR spectroscopy Methods 0.000 description 8
• XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 8
• ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 8
• 229940093475 2-ethoxyethanol Drugs 0.000 description 8
• 239000005711 Benzoic acid Substances 0.000 description 8
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 8
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 8
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 8
• 235000010233 benzoic acid Nutrition 0.000 description 8
• 150000001879 copper Chemical class 0.000 description 8
• 239000010949 copper Substances 0.000 description 8
• QKZWXPLBVCKXNQ-ROJLCIKYSA-N dipamp Chemical compound COC1=CC=CC=C1[P@@](C=1C=CC=CC=1)CC[P@@](C=1C(=CC=CC=1)OC)C1=CC=CC=C1 QKZWXPLBVCKXNQ-ROJLCIKYSA-N 0.000 description 8
• MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 description 8
• 150000002148 esters Chemical class 0.000 description 8
• WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 8
• GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 8
• GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 8
• FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 8
• JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 8
• 229940011051 isopropyl acetate Drugs 0.000 description 8
• GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 8
• OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 8
• 150000002815 nickel Chemical class 0.000 description 8
• WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 8
• 238000010992 reflux Methods 0.000 description 8
• 238000000638 solvent extraction Methods 0.000 description 8
• 235000002906 tartaric acid Nutrition 0.000 description 8
• JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
• NKTDEOHJLYPGQC-UHFFFAOYSA-N 2-acetyl-n-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)C)=NC=C1C(=O)NC1=CC(C(F)(F)F)=C(Cl)C=N1 NKTDEOHJLYPGQC-UHFFFAOYSA-N 0.000 description 7
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 7
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 7
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 7
• 150000003863 ammonium salts Chemical class 0.000 description 7
• 239000013078 crystal Substances 0.000 description 7
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 7
• OUQSAXROROGQEE-QFIPXVFZSA-N diphenyl-[2-[(4r)-4-propan-2-yl-4,5-dihydro-1,3-oxazol-2-yl]phenyl]phosphane Chemical compound CC(C)[C@@H]1COC(C=2C(=CC=CC=2)P(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 OUQSAXROROGQEE-QFIPXVFZSA-N 0.000 description 7
• 239000011521 glass Substances 0.000 description 7
• 239000000463 material Substances 0.000 description 7
• 239000000843 powder Substances 0.000 description 7
• 239000002244 precipitate Substances 0.000 description 7
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
• 235000017557 sodium bicarbonate Nutrition 0.000 description 7
• MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 6
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 6
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 6
• BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 6
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 6
• 239000004475 Arginine Substances 0.000 description 6
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
• WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 6
• AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 6
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 6
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 6
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 6
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 6
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 6
• 239000004472 Lysine Substances 0.000 description 6
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
• AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 6
• UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 6
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 6
• LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 6
• 150000007513 acids Chemical class 0.000 description 6
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 6
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 6
• 238000010976 amide bond formation reaction Methods 0.000 description 6
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 6
• 125000005129 aryl carbonyl group Chemical group 0.000 description 6
• 235000003704 aspartic acid Nutrition 0.000 description 6
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 6
• 229940092714 benzenesulfonic acid Drugs 0.000 description 6
• OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 6
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 6
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 6
• 239000012320 chlorinating reagent Substances 0.000 description 6
• 125000003963 dichloro group Chemical group Cl* 0.000 description 6
• 239000000539 dimer Substances 0.000 description 6
• ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
• KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 6
• 239000001530 fumaric acid Substances 0.000 description 6
• 235000011087 fumaric acid Nutrition 0.000 description 6
• 239000004220 glutamic acid Substances 0.000 description 6
• 235000013922 glutamic acid Nutrition 0.000 description 6
• 238000004896 high resolution mass spectrometry Methods 0.000 description 6
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 6
• 229940071870 hydroiodic acid Drugs 0.000 description 6
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
• 239000011976 maleic acid Substances 0.000 description 6
• 239000001630 malic acid Substances 0.000 description 6
• 235000011090 malic acid Nutrition 0.000 description 6
• 229940098779 methanesulfonic acid Drugs 0.000 description 6
• 150000007522 mineralic acids Chemical class 0.000 description 6
• 239000002808 molecular sieve Substances 0.000 description 6
• 229910017604 nitric acid Inorganic materials 0.000 description 6
• 229960003104 ornithine Drugs 0.000 description 6
• 235000006408 oxalic acid Nutrition 0.000 description 6
• 229910052698 phosphorus Inorganic materials 0.000 description 6
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 6
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 6
• ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 6
• NTOIKDYVJIWVSU-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioic acid Chemical compound C1=CC(C)=CC=C1C(=O)C(O)(C(O)=O)C(O)(C(O)=O)C(=O)C1=CC=C(C)C=C1 NTOIKDYVJIWVSU-UHFFFAOYSA-N 0.000 description 5
• MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
• 239000004215 Carbon black (E152) Substances 0.000 description 5
• 229910019142 PO4 Inorganic materials 0.000 description 5
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
• 150000001242 acetic acid derivatives Chemical class 0.000 description 5
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
• 150000001340 alkali metals Chemical class 0.000 description 5
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
• 150000001412 amines Chemical class 0.000 description 5
• 150000004982 aromatic amines Chemical class 0.000 description 5
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 5
• 229910000024 caesium carbonate Inorganic materials 0.000 description 5
• HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 5
• 150000004649 carbonic acid derivatives Chemical class 0.000 description 5
• 150000001735 carboxylic acids Chemical class 0.000 description 5
• IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 5
• 229940043279 diisopropylamine Drugs 0.000 description 5
• 229910000396 dipotassium phosphate Inorganic materials 0.000 description 5
• 235000019797 dipotassium phosphate Nutrition 0.000 description 5
• BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 5
• 229930195733 hydrocarbon Natural products 0.000 description 5
• 229910052500 inorganic mineral Inorganic materials 0.000 description 5
• JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 5
• AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 description 5
• MXIRPJHGXWFUAE-UHFFFAOYSA-N lithium;propan-1-olate Chemical compound [Li+].CCC[O-] MXIRPJHGXWFUAE-UHFFFAOYSA-N 0.000 description 5
• HAUKUGBTJXWQMF-UHFFFAOYSA-N lithium;propan-2-olate Chemical compound [Li+].CC(C)[O-] HAUKUGBTJXWQMF-UHFFFAOYSA-N 0.000 description 5
• 235000010755 mineral Nutrition 0.000 description 5
• 239000011707 mineral Substances 0.000 description 5
• KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 5
• 235000021317 phosphate Nutrition 0.000 description 5
• 150000003013 phosphoric acid derivatives Chemical class 0.000 description 5
• 235000011056 potassium acetate Nutrition 0.000 description 5
• 235000015497 potassium bicarbonate Nutrition 0.000 description 5
• 229910000028 potassium bicarbonate Inorganic materials 0.000 description 5
• 239000011736 potassium bicarbonate Substances 0.000 description 5
• 229910000027 potassium carbonate Inorganic materials 0.000 description 5
• 235000011181 potassium carbonates Nutrition 0.000 description 5
• RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 5
• TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 5
• 229940086066 potassium hydrogencarbonate Drugs 0.000 description 5
• BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 5
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
• AWDMDDKZURRKFG-UHFFFAOYSA-N potassium;propan-1-olate Chemical compound [K+].CCC[O-] AWDMDDKZURRKFG-UHFFFAOYSA-N 0.000 description 5
• WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 5
• 239000000047 product Substances 0.000 description 5
• 239000001632 sodium acetate Substances 0.000 description 5
• 235000017281 sodium acetate Nutrition 0.000 description 5
• 229910000029 sodium carbonate Inorganic materials 0.000 description 5
• QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 5
• RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 5
• 239000001488 sodium phosphate Substances 0.000 description 5
• 229910000162 sodium phosphate Inorganic materials 0.000 description 5
• RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 5
• WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 5
• 150000003460 sulfonic acids Chemical class 0.000 description 5
• 238000012546 transfer Methods 0.000 description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
• 229910000404 tripotassium phosphate Inorganic materials 0.000 description 5
• 235000019798 tripotassium phosphate Nutrition 0.000 description 5
• RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 5
• LYHOBZAADXPPNW-UHFFFAOYSA-N (r)-xylyl-phanephos Chemical compound CC1=CC(C)=CC(P(C=2C=C(C)C=C(C)C=2)C=2C=3CCC4=CC=C(C(=C4)P(C=4C=C(C)C=C(C)C=4)C=4C=C(C)C=C(C)C=4)CCC(=CC=3)C=2)=C1 LYHOBZAADXPPNW-UHFFFAOYSA-N 0.000 description 4
• XUJAXBFFTHRXLV-UHFFFAOYSA-N 185449-81-4 Chemical compound C1COCCN1P1OC(C=CC=2C3=CC=CC=2)=C3C(C2=CC=CC=C2C=C2)=C2O1 XUJAXBFFTHRXLV-UHFFFAOYSA-N 0.000 description 4
• OVDOTYJKKSGNGE-RXMQYKEDSA-N 2-[(1r)-1-aminoethyl]-n-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound S1C([C@H](N)C)=NC=C1C(=O)NC1=CC(C(F)(F)F)=C(Cl)C=N1 OVDOTYJKKSGNGE-RXMQYKEDSA-N 0.000 description 4
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 4
• 239000002841 Lewis acid Substances 0.000 description 4
• VWMJHAFYPMOMGF-ZCFIWIBFSA-N TAK-580 Chemical compound N([C@H](C)C=1SC(=CN=1)C(=O)NC=1N=CC(Cl)=C(C=1)C(F)(F)F)C(=O)C1=NC=NC(N)=C1Cl VWMJHAFYPMOMGF-ZCFIWIBFSA-N 0.000 description 4
• MXGXXBYVDMVJAO-UHFFFAOYSA-N [1-[2-bis(3,5-dimethylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical group CC1=CC(C)=CC(P(C=2C=C(C)C=C(C)C=2)C=2C(=C3C=CC=CC3=CC=2)C=2C3=CC=CC=C3C=CC=2P(C=2C=C(C)C=C(C)C=2)C=2C=C(C)C=C(C)C=2)=C1 MXGXXBYVDMVJAO-UHFFFAOYSA-N 0.000 description 4
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
• 125000003342 alkenyl group Chemical group 0.000 description 4
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
• 238000004296 chiral HPLC Methods 0.000 description 4
• 150000004985 diamines Chemical class 0.000 description 4
• DHCWLIOIJZJFJE-UHFFFAOYSA-L dichlororuthenium Chemical compound Cl[Ru]Cl DHCWLIOIJZJFJE-UHFFFAOYSA-L 0.000 description 4
• 238000010438 heat treatment Methods 0.000 description 4
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
• 150000007517 lewis acids Chemical class 0.000 description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 description 4
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
• 150000007524 organic acids Chemical class 0.000 description 4
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
• VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
• 125000004437 phosphorous atom Chemical group 0.000 description 4
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
• MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 4
• 229960004889 salicylic acid Drugs 0.000 description 4
• 239000011877 solvent mixture Substances 0.000 description 4
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
• VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 4
• 239000011592 zinc chloride Substances 0.000 description 4
• 235000005074 zinc chloride Nutrition 0.000 description 4
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 3
• SYTBZMRGLBWNTM-SNVBAGLBSA-N (R)-flurbiprofen Chemical compound FC1=CC([C@H](C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-SNVBAGLBSA-N 0.000 description 3
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 3
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
• LGKSZMHBIKHZQG-YPXUMCKCSA-N 2-[(E)-N-benzamido-C-methylcarbonimidoyl]-N-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound C(C1=CC=CC=C1)(=O)N\N=C(/C)\C=1SC(=CN=1)C(=O)NC1=NC=C(C(=C1)C(F)(F)F)Cl LGKSZMHBIKHZQG-YPXUMCKCSA-N 0.000 description 3
• MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
• CTYPJIUQROQJBG-UHFFFAOYSA-N 4-diphenylphosphanylpentan-2-yl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)CC(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 CTYPJIUQROQJBG-UHFFFAOYSA-N 0.000 description 3
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
• 125000004414 alkyl thio group Chemical group 0.000 description 3
• 125000005116 aryl carbamoyl group Chemical group 0.000 description 3
• XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 3
• HGTBZFMPHBAUCQ-KHZPMNTOSA-N cyclopentane;dicyclohexyl-[(1r)-1-(2-diphenylphosphanylcyclopentyl)ethyl]phosphane;iron Chemical compound [Fe].[CH]1[CH][CH][CH][CH]1.[C]1([C@@H](C)P(C2CCCCC2)C2CCCCC2)[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1 HGTBZFMPHBAUCQ-KHZPMNTOSA-N 0.000 description 3
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
• 230000005595 deprotonation Effects 0.000 description 3
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
• WUOIAOOSKMHJOV-UHFFFAOYSA-N ethyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CC)C1=CC=CC=C1 WUOIAOOSKMHJOV-UHFFFAOYSA-N 0.000 description 3
• 125000005844 heterocyclyloxy group Chemical group 0.000 description 3
• 239000000852 hydrogen donor Substances 0.000 description 3
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 3
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
• 125000002883 imidazolyl group Chemical group 0.000 description 3
• 230000003993 interaction Effects 0.000 description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
• 239000007788 liquid Substances 0.000 description 3
• PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
• SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 3
• 125000004430 oxygen atom Chemical group O* 0.000 description 3
• 238000003756 stirring Methods 0.000 description 3
• 238000006467 substitution reaction Methods 0.000 description 3
• 125000004434 sulfur atom Chemical group 0.000 description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
• 238000005406 washing Methods 0.000 description 3
• ZFVHFEXIVQSRNV-QMDOQEJBSA-N (1z,5z)-cycloocta-1,5-diene;iridium;tetrafluoroborate Chemical compound [Ir].F[B-](F)(F)F.C\1C\C=C/CC\C=C/1.C\1C\C=C/CC\C=C/1 ZFVHFEXIVQSRNV-QMDOQEJBSA-N 0.000 description 2
• ZFOUGNAJKPZBPO-AUUWQFPRSA-N (1z,5z)-cycloocta-1,5-diene;iridium;tetrakis[3,5-bis(trifluoromethyl)phenyl]boranuide Chemical compound [Ir].C\1C\C=C/CC\C=C/1.C\1C\C=C/CC\C=C/1.FC(F)(F)C1=CC(C(F)(F)F)=CC([B-](C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C1 ZFOUGNAJKPZBPO-AUUWQFPRSA-N 0.000 description 2
• QKZWXPLBVCKXNQ-UHFFFAOYSA-N (2-methoxyphenyl)-[2-[(2-methoxyphenyl)-phenylphosphanyl]ethyl]-phenylphosphane Chemical compound COC1=CC=CC=C1P(C=1C=CC=CC=1)CCP(C=1C(=CC=CC=1)OC)C1=CC=CC=C1 QKZWXPLBVCKXNQ-UHFFFAOYSA-N 0.000 description 2
• WDYGPMAMBXJESZ-GOSISDBHSA-N (2r)-1,1-bis(4-methoxyphenyl)-3-methylbutane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1C(N)([C@H](N)C(C)C)C1=CC=C(OC)C=C1 WDYGPMAMBXJESZ-GOSISDBHSA-N 0.000 description 2
• AJNZWRKTWQLAJK-KLHDSHLOSA-N (2r,5r)-1-[2-[(2r,5r)-2,5-dimethylphospholan-1-yl]phenyl]-2,5-dimethylphospholane Chemical compound C[C@@H]1CC[C@@H](C)P1C1=CC=CC=C1P1[C@H](C)CC[C@H]1C AJNZWRKTWQLAJK-KLHDSHLOSA-N 0.000 description 2
• MIOPJNTWMNEORI-XVKPBYJWSA-N (R)-camphorsulfonic acid Chemical compound C1C[C@]2(CS(O)(=O)=O)C(=O)C[C@H]1C2(C)C MIOPJNTWMNEORI-XVKPBYJWSA-N 0.000 description 2
• GTIXSUJKFAATAE-UHFFFAOYSA-N (r)-c3-tunephos Chemical compound C=12C(C(=CC=C3)P(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3OCCCOC2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 GTIXSUJKFAATAE-UHFFFAOYSA-N 0.000 description 2
• SSUJUUNLZQVZMO-UHFFFAOYSA-N 1,2,3,4,8,9,10,10a-octahydropyrimido[1,2-a]azepine Chemical compound C1CCC=CN2CCCNC21 SSUJUUNLZQVZMO-UHFFFAOYSA-N 0.000 description 2
• PONXTPCRRASWKW-UHFFFAOYSA-N 1,2-diphenylethane-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)C(N)C1=CC=CC=C1 PONXTPCRRASWKW-UHFFFAOYSA-N 0.000 description 2
• WYMIZOFPJKBCLJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-[(4-methoxyphenyl)methyl]-4-methylpentane-2,3-diamine Chemical compound C1=CC(OC)=CC=C1CC(N)(C(N)C(C)C)CC1=CC=C(OC)C=C1 WYMIZOFPJKBCLJ-UHFFFAOYSA-N 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• IJDORVLZCGYHFA-OAHLLOKOSA-N 2-[(1R)-1-(benzhydrylamino)ethyl]-N-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound C1(=C(C=C(N=C1)NC(=O)C1=CN=C(S1)[C@@H](C)NC(C1=CC=CC=C1)C1=CC=CC=C1)C(F)(F)F)Cl IJDORVLZCGYHFA-OAHLLOKOSA-N 0.000 description 2
• LMXKKBKOISJHCT-OAHLLOKOSA-N 2-[(1R)-1-[bis(4-methoxyphenyl)methylamino]ethyl]-N-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound C1=C(C(=CC(=N1)NC(=O)C1=CN=C(S1)[C@@H](C)NC(C1=CC=C(OC)C=C1)C1=CC=C(OC)C=C1)C(F)(F)F)Cl LMXKKBKOISJHCT-OAHLLOKOSA-N 0.000 description 2
• BHCGAJKJTLJQPV-NUBCRITNSA-N 2-[(1R)-1-aminoethyl]-N-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-1,3-thiazole-5-carboxamide hydrochloride Chemical compound Cl.N[C@H](C)C=1SC(=CN=1)C(=O)NC1=NC=C(C(=C1)C(F)(F)F)Cl BHCGAJKJTLJQPV-NUBCRITNSA-N 0.000 description 2
• IAWQBPIGKCPCRU-JTQLQIEISA-N 2-[(1S)-1-(2-benzoylhydrazinyl)ethyl]-N-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound C(C1=CC=CC=C1)(=O)NN[C@@H](C)C=1SC(=CN=1)C(=O)NC1=NC=C(C(=C1)C(F)(F)F)Cl IAWQBPIGKCPCRU-JTQLQIEISA-N 0.000 description 2
• BURBNIPKSRJAIQ-UHFFFAOYSA-N 2-azaniumyl-3-[3-(trifluoromethyl)phenyl]propanoate Chemical group OC(=O)C(N)CC1=CC=CC(C(F)(F)F)=C1 BURBNIPKSRJAIQ-UHFFFAOYSA-N 0.000 description 2
• NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
• XIEDAMQXYCHOHG-UHFFFAOYSA-N 6-amino-5-chloropyrimidine-4-carboxylic acid Chemical compound NC1=NC=NC(C(O)=O)=C1Cl XIEDAMQXYCHOHG-UHFFFAOYSA-N 0.000 description 2
• KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
• DCPGIKNMLWEMQT-BHGWPJFGSA-N C(C1=CC=CC=C1)\N=C(/C)\C=1SC(=CN=1)C(=O)NC1=NC=C(C(=C1)C(F)(F)F)Cl Chemical compound C(C1=CC=CC=C1)\N=C(/C)\C=1SC(=CN=1)C(=O)NC1=NC=C(C(=C1)C(F)(F)F)Cl DCPGIKNMLWEMQT-BHGWPJFGSA-N 0.000 description 2
• BNNDCCUQINXYIN-VWJSQJICSA-N C1=C(C(=CC(=N1)NC(=O)C1=CN=C(S1)/C(=N/C(C1=CC=CC=C1)C1=CC=CC=C1)/C)C(F)(F)F)Cl Chemical compound C1=C(C(=CC(=N1)NC(=O)C1=CN=C(S1)/C(=N/C(C1=CC=CC=C1)C1=CC=CC=C1)/C)C(F)(F)F)Cl BNNDCCUQINXYIN-VWJSQJICSA-N 0.000 description 2
• 125000005914 C6-C14 aryloxy group Chemical group 0.000 description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
• LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
• OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
• DIIWSYPKAJVXBV-UHFFFAOYSA-N Hantzch dihydropyridine Natural products CCOC(=O)C1=CC(C(=O)OCC)=C(C)N=C1C DIIWSYPKAJVXBV-UHFFFAOYSA-N 0.000 description 2
• KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
• 150000001216 Samarium Chemical class 0.000 description 2
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
• 101001081574 Xenopus laevis DNA-binding protein inhibitor ID-2-A Proteins 0.000 description 2
• 101001036283 Xenopus laevis DNA-binding protein inhibitor ID-3-A Proteins 0.000 description 2
• 101100020289 Xenopus laevis koza gene Proteins 0.000 description 2
• ANSOKCGDSQQISA-UHFFFAOYSA-N [1-(2-diphenylphosphanyl-5,6,7,8-tetrahydronaphthalen-1-yl)-5,6,7,8-tetrahydronaphthalen-2-yl]-diphenylphosphane Chemical group C1CCCC(C=2C=3C(=CC=C4CCCCC4=3)P(C=3C=CC=CC=3)C=3C=CC=CC=3)=C1C=CC=2P(C=1C=CC=CC=1)C1=CC=CC=C1 ANSOKCGDSQQISA-UHFFFAOYSA-N 0.000 description 2
• ZGKACHAOHYORST-UHFFFAOYSA-N [1-[2-bis(2,6-dimethylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(2,6-dimethylphenyl)phosphane Chemical compound CC1=CC=CC(C)=C1P(C=1C(=CC=CC=1C)C)C1=CC=C(C=CC=C2)C2=C1C1=C(P(C=2C(=CC=CC=2C)C)C=2C(=CC=CC=2C)C)C=CC2=CC=CC=C12 ZGKACHAOHYORST-UHFFFAOYSA-N 0.000 description 2
• ZNORAFJUESSLTM-UHFFFAOYSA-N [4-[5-bis(3,5-ditert-butyl-4-methoxyphenyl)phosphanyl-1,3-benzodioxol-4-yl]-1,3-benzodioxol-5-yl]-bis(3,5-ditert-butyl-4-methoxyphenyl)phosphane Chemical compound C1=C(C(C)(C)C)C(OC)=C(C(C)(C)C)C=C1P(C=1C(=C2OCOC2=CC=1)C=1C(=CC=C2OCOC2=1)P(C=1C=C(C(OC)=C(C=1)C(C)(C)C)C(C)(C)C)C=1C=C(C(OC)=C(C=1)C(C)(C)C)C(C)(C)C)C1=CC(C(C)(C)C)=C(OC)C(C(C)(C)C)=C1 ZNORAFJUESSLTM-UHFFFAOYSA-N 0.000 description 2
• XBJFCYDKBDVADW-UHFFFAOYSA-N acetonitrile;formic acid Chemical compound CC#N.OC=O XBJFCYDKBDVADW-UHFFFAOYSA-N 0.000 description 2
• FGDQGIKMWOAFIK-UHFFFAOYSA-N acetonitrile;phosphoric acid Chemical compound CC#N.OP(O)(O)=O FGDQGIKMWOAFIK-UHFFFAOYSA-N 0.000 description 2
• 125000005595 acetylacetonate group Chemical group 0.000 description 2
• 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 2
• 125000003282 alkyl amino group Chemical group 0.000 description 2
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 2
• AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
• 238000005576 amination reaction Methods 0.000 description 2
• 229940063284 ammonium salicylate Drugs 0.000 description 2
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
• 125000001691 aryl alkyl amino group Chemical group 0.000 description 2
• 125000002102 aryl alkyloxo group Chemical group 0.000 description 2
• 125000001769 aryl amino group Chemical group 0.000 description 2
• 125000004658 aryl carbonyl amino group Chemical group 0.000 description 2
• 125000005199 aryl carbonyloxy group Chemical group 0.000 description 2
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 2
• 125000004657 aryl sulfonyl amino group Chemical group 0.000 description 2
• 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 2
• 238000010923 batch production Methods 0.000 description 2
• WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 description 2
• RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
• 239000012965 benzophenone Substances 0.000 description 2
• 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 2
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
• 239000012267 brine Substances 0.000 description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 150000001718 carbodiimides Chemical class 0.000 description 2
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
• 239000003153 chemical reaction reagent Substances 0.000 description 2
• 150000001868 cobalt Chemical class 0.000 description 2
• 238000010924 continuous production Methods 0.000 description 2
• 125000000392 cycloalkenyl group Chemical group 0.000 description 2
• 125000000000 cycloalkoxy group Chemical group 0.000 description 2
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
• LJXTYJXBORAIHX-UHFFFAOYSA-N diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1 LJXTYJXBORAIHX-UHFFFAOYSA-N 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 2
• LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 2
• 125000006125 ethylsulfonyl group Chemical group 0.000 description 2
• 238000004508 fractional distillation Methods 0.000 description 2
• 150000002343 gold Chemical class 0.000 description 2
• 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
• 150000002466 imines Chemical class 0.000 description 2
• 239000010422 internal standard material Substances 0.000 description 2
• JJNVAYCGZVUOFH-UHFFFAOYSA-N iridium;methanol Chemical compound [Ir].OC JJNVAYCGZVUOFH-UHFFFAOYSA-N 0.000 description 2
• 150000002505 iron Chemical class 0.000 description 2
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
• 238000002955 isolation Methods 0.000 description 2
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
• 229910052987 metal hydride Inorganic materials 0.000 description 2
• 150000004681 metal hydrides Chemical class 0.000 description 2
• 125000005394 methallyl group Chemical group 0.000 description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
• 239000012046 mixed solvent Substances 0.000 description 2
• 125000002950 monocyclic group Chemical group 0.000 description 2
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• 150000002894 organic compounds Chemical class 0.000 description 2
• 150000002907 osmium Chemical class 0.000 description 2
• 125000000160 oxazolidinyl group Chemical group 0.000 description 2
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
• XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 2
• 150000008300 phosphoramidites Chemical class 0.000 description 2
• 239000011574 phosphorus Substances 0.000 description 2
• 150000003057 platinum Chemical class 0.000 description 2
• 125000003367 polycyclic group Chemical group 0.000 description 2
• 229960003975 potassium Drugs 0.000 description 2
• 239000011591 potassium Substances 0.000 description 2
• 229910052700 potassium Inorganic materials 0.000 description 2
• CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 2
• 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 238000000746 purification Methods 0.000 description 2
• 125000005554 pyridyloxy group Chemical group 0.000 description 2
• HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 description 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
• 239000002994 raw material Substances 0.000 description 2
• YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 2
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
• 150000003378 silver Chemical class 0.000 description 2
• 229910052938 sodium sulfate Inorganic materials 0.000 description 2
• 235000011152 sodium sulphate Nutrition 0.000 description 2
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
• 239000010421 standard material Substances 0.000 description 2
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
• 150000003892 tartrate salts Chemical class 0.000 description 2
• HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
• 150000003608 titanium Chemical class 0.000 description 2
• XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
• 150000003623 transition metal compounds Chemical class 0.000 description 2
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 2
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 239000003643 water by type Substances 0.000 description 2
• 150000003751 zinc Chemical class 0.000 description 2
• 229940102001 zinc bromide Drugs 0.000 description 2
• MDAHANCDXSBKPT-UHFFFAOYSA-N (1-cyclohexyl-2-diphenylphosphanylethyl)-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CC(P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1CCCCC1 MDAHANCDXSBKPT-UHFFFAOYSA-N 0.000 description 1
• YMJAIEYASUCCMJ-UHFFFAOYSA-N (1-isoquinolin-1-ylnaphthalen-2-yl)-diphenylphosphane Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CN=1)C1=CC=CC=C1 YMJAIEYASUCCMJ-UHFFFAOYSA-N 0.000 description 1
• NXLACVVNHYIYJN-ZIAGYGMSSA-N (1r)-1-phenyl-n-[(1r)-1-phenylethyl]ethanamine Chemical compound C1([C@@H](C)N[C@H](C)C=2C=CC=CC=2)=CC=CC=C1 NXLACVVNHYIYJN-ZIAGYGMSSA-N 0.000 description 1
• RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
• GVVCHDNSTMEUCS-UAFMIMERSA-N (2r,5r)-1-[2-[(2r,5r)-2,5-diethylphospholan-1-yl]phenyl]-2,5-diethylphospholane Chemical compound CC[C@@H]1CC[C@@H](CC)P1C1=CC=CC=C1P1[C@H](CC)CC[C@H]1CC GVVCHDNSTMEUCS-UAFMIMERSA-N 0.000 description 1
• CDJHPMXMJUCLPA-UHFFFAOYSA-N (3-diphenylphosphanyl-2-bicyclo[2.2.1]hept-5-enyl)-diphenylphosphane Chemical compound C1C2C=CC1C(P(C=1C=CC=CC=1)C=1C=CC=CC=1)C2P(C=1C=CC=CC=1)C1=CC=CC=C1 CDJHPMXMJUCLPA-UHFFFAOYSA-N 0.000 description 1
• XQXSISPADQWFER-UHFFFAOYSA-M (4,6-dimethoxy-1,3,5-triazin-2-yl)-dimethyl-(2-octoxy-2-oxoethyl)azanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CCCCCCCCOC(=O)C[N+](C)(C)C1=NC(OC)=NC(OC)=N1 XQXSISPADQWFER-UHFFFAOYSA-M 0.000 description 1
• 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 description 1
• 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 description 1
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
• IWYDHOAUDWTVEP-ZETCQYMHSA-M (S)-mandelate Chemical compound [O-]C(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-M 0.000 description 1
• DRZBLHZZDMCPGX-VXKWHMMOSA-N (r)-tert-butyl-[3-[tert-butyl(methyl)phosphanyl]quinoxalin-2-yl]-methylphosphane Chemical compound C1=CC=C2N=C([P@](C)C(C)(C)C)C([P@](C)C(C)(C)C)=NC2=C1 DRZBLHZZDMCPGX-VXKWHMMOSA-N 0.000 description 1
• SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
• CJLVEEKBJGYLAZ-UHFFFAOYSA-N 1,1-dinaphthalen-1-ylpropane-1,2-diamine Chemical compound C1=CC=C2C(C(N)(C=3C4=CC=CC=C4C=CC=3)C(N)C)=CC=CC2=C1 CJLVEEKBJGYLAZ-UHFFFAOYSA-N 0.000 description 1
• OWUQWDCZCOJEKU-UHFFFAOYSA-N 1,1-diphenylpropane-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)(C(N)C)C1=CC=CC=C1 OWUQWDCZCOJEKU-UHFFFAOYSA-N 0.000 description 1
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
• 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
• 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
• GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
• 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 1
• 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
• BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
• BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 1
• OLEZPCNZPBVPOY-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-[(4-methoxyphenyl)methyl]-4-phenylbutane-2,3-diamine Chemical compound C1=CC(OC)=CC=C1CC(N)(C(N)CC=1C=CC=CC=1)CC1=CC=C(OC)C=C1 OLEZPCNZPBVPOY-UHFFFAOYSA-N 0.000 description 1
• PILUMYUEADKHRE-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-[(4-methoxyphenyl)methyl]-5-methylhexane-2,3-diamine Chemical compound C1=CC(OC)=CC=C1CC(N)(C(N)CC(C)C)CC1=CC=C(OC)C=C1 PILUMYUEADKHRE-UHFFFAOYSA-N 0.000 description 1
• DJIULQYRGPDJQJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-[(4-methoxyphenyl)methyl]butane-2,3-diamine Chemical compound C1=CC(OC)=CC=C1CC(N)(C(C)N)CC1=CC=C(OC)C=C1 DJIULQYRGPDJQJ-UHFFFAOYSA-N 0.000 description 1
• IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 1
• HHAISVSEJFEWBZ-UHFFFAOYSA-N 1-[4-(trifluoromethyl)phenyl]ethanone Chemical compound CC(=O)C1=CC=C(C(F)(F)F)C=C1 HHAISVSEJFEWBZ-UHFFFAOYSA-N 0.000 description 1
• MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
• 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
• 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
• WGOBPPNNYVSJTE-UHFFFAOYSA-N 1-diphenylphosphanylpropan-2-yl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)CP(C=1C=CC=CC=1)C1=CC=CC=C1 WGOBPPNNYVSJTE-UHFFFAOYSA-N 0.000 description 1
• 125000006039 1-hexenyl group Chemical group 0.000 description 1
• FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 1
• PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 1
• 125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
• 125000006023 1-pentenyl group Chemical group 0.000 description 1
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 125000006017 1-propenyl group Chemical group 0.000 description 1
• 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
• UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
• WOHLSTOWRAOMSG-UHFFFAOYSA-N 2,3-dihydro-1,3-benzothiazole Chemical compound C1=CC=C2SCNC2=C1 WOHLSTOWRAOMSG-UHFFFAOYSA-N 0.000 description 1
• CCIUQRKCMXXTOI-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(4-methoxybenzoyl)butanedioic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C(O)(C(O)=O)C(O)(C(O)=O)C(=O)C1=CC=C(OC)C=C1 CCIUQRKCMXXTOI-UHFFFAOYSA-N 0.000 description 1
• JITRCUREWFPMMJ-UHFFFAOYSA-N 2,3-dimethylbutane-1,1-diamine Chemical compound CC(C)C(C)C(N)N JITRCUREWFPMMJ-UHFFFAOYSA-N 0.000 description 1
• JFJNVIPVOCESGZ-UHFFFAOYSA-N 2,3-dipyridin-2-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 JFJNVIPVOCESGZ-UHFFFAOYSA-N 0.000 description 1
• IAWQBPIGKCPCRU-SNVBAGLBSA-N 2-[(1R)-1-(2-benzoylhydrazinyl)ethyl]-N-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound C(C1=CC=CC=C1)(=O)NN[C@H](C)C=1SC(=CN=1)C(=O)NC1=NC=C(C(=C1)C(F)(F)F)Cl IAWQBPIGKCPCRU-SNVBAGLBSA-N 0.000 description 1
• BGFQYXMJCOHLMC-NUBCRITNSA-N 2-[(1R)-1-aminoethyl]-N-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-1,3-thiazole-5-carboxamide hydrobromide Chemical compound Br.N[C@H](C)C=1SC(=CN1)C(=O)NC1=NC=C(C(=C1)C(F)(F)F)Cl BGFQYXMJCOHLMC-NUBCRITNSA-N 0.000 description 1
• BHCGAJKJTLJQPV-JEDNCBNOSA-N 2-[(1S)-1-aminoethyl]-N-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-1,3-thiazole-5-carboxamide hydrochloride Chemical compound Cl.N[C@@H](C)C=1SC(=CN1)C(=O)NC1=NC=C(C(=C1)C(F)(F)F)Cl BHCGAJKJTLJQPV-JEDNCBNOSA-N 0.000 description 1
• QHPINLPOZOFRCQ-UHFFFAOYSA-N 2-[1-(benzylamino)ethyl]-N-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound N1=CC(=C(C=C1NC(=O)C1=CN=C(S1)C(C)NCC1=CC=CC=C1)C(F)(F)F)Cl QHPINLPOZOFRCQ-UHFFFAOYSA-N 0.000 description 1
• LIFGFPYQXSGAQL-UHFFFAOYSA-N 2-acetyl-1,3-thiazole-5-carboxylic acid Chemical compound CC(=O)C1=NC=C(C(O)=O)S1 LIFGFPYQXSGAQL-UHFFFAOYSA-N 0.000 description 1
• KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 1
• 125000005999 2-bromoethyl group Chemical group 0.000 description 1
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
• 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
• 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
• XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
• 125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 description 1
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
• 125000006024 2-pentenyl group Chemical group 0.000 description 1
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
• FQBFZYRWDRXSDM-UHFFFAOYSA-N 2H-1,5-dioxonine Chemical compound O1CC=COC=CC=C1 FQBFZYRWDRXSDM-UHFFFAOYSA-N 0.000 description 1
• 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
• 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
• FWXAUDSWDBGCMN-UHFFFAOYSA-N 3-diphenylphosphanylbutan-2-yl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 FWXAUDSWDBGCMN-UHFFFAOYSA-N 0.000 description 1
• 125000006041 3-hexenyl group Chemical group 0.000 description 1
• WMOCSBSDPNLVAZ-UHFFFAOYSA-N 3-methyl-1,1-dinaphthalen-1-ylbutane-1,2-diamine Chemical compound C1=CC=C2C(C(N)(C=3C4=CC=CC=C4C=CC=3)C(N)C(C)C)=CC=CC2=C1 WMOCSBSDPNLVAZ-UHFFFAOYSA-N 0.000 description 1
• UGYCWJKLMOREKO-UHFFFAOYSA-N 3-methyl-1,1-diphenylbutane-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)(C(N)C(C)C)C1=CC=CC=C1 UGYCWJKLMOREKO-UHFFFAOYSA-N 0.000 description 1
• BMTZEAOGFDXDAD-UHFFFAOYSA-M 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium;chloride Chemical compound [Cl-].COC1=NC(OC)=NC([N+]2(C)CCOCC2)=N1 BMTZEAOGFDXDAD-UHFFFAOYSA-M 0.000 description 1
• XZKIHKMTEMTJQX-UHFFFAOYSA-N 4-Nitrophenyl Phosphate Chemical compound OP(O)(=O)OC1=CC=C([N+]([O-])=O)C=C1 XZKIHKMTEMTJQX-UHFFFAOYSA-N 0.000 description 1
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
• FTBSUYHLNOXVAC-UHFFFAOYSA-N 4-[[1-[2-bis[4-(diethylamino)phenyl]phosphanylnaphthalen-1-yl]naphthalen-2-yl]-[4-(diethylamino)phenyl]phosphanyl]-n,n-diethylaniline Chemical group C1=CC(N(CC)CC)=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC(=CC=1)N(CC)CC)C=1C=CC(=CC=1)N(CC)CC)C1=CC=C(N(CC)CC)C=C1 FTBSUYHLNOXVAC-UHFFFAOYSA-N 0.000 description 1
• QZZHBRLYFGWAGC-UHFFFAOYSA-N 4-[[1-[2-bis[4-(dimethylamino)-3,5-di(propan-2-yl)phenyl]phosphanylnaphthalen-1-yl]naphthalen-2-yl]-[4-(dimethylamino)-3,5-di(propan-2-yl)phenyl]phosphanyl]-n,n-dimethyl-2,6-di(propan-2-yl)aniline Chemical group CC(C)C1=C(N(C)C)C(C(C)C)=CC(P(C=2C=C(C(N(C)C)=C(C(C)C)C=2)C(C)C)C=2C(=C3C=CC=CC3=CC=2)C=2C3=CC=CC=C3C=CC=2P(C=2C=C(C(N(C)C)=C(C(C)C)C=2)C(C)C)C=2C=C(C(N(C)C)=C(C(C)C)C=2)C(C)C)=C1 QZZHBRLYFGWAGC-UHFFFAOYSA-N 0.000 description 1
• OHWNWPBVLQUALU-UHFFFAOYSA-N 4-[[1-[2-bis[4-(dimethylamino)-3,5-diethylphenyl]phosphanylnaphthalen-1-yl]naphthalen-2-yl]-[4-(dimethylamino)-3,5-diethylphenyl]phosphanyl]-2,6-diethyl-n,n-dimethylaniline Chemical group CCC1=C(N(C)C)C(CC)=CC(P(C=2C=C(CC)C(N(C)C)=C(CC)C=2)C=2C(=C3C=CC=CC3=CC=2)C=2C3=CC=CC=C3C=CC=2P(C=2C=C(CC)C(N(C)C)=C(CC)C=2)C=2C=C(CC)C(N(C)C)=C(CC)C=2)=C1 OHWNWPBVLQUALU-UHFFFAOYSA-N 0.000 description 1
• KXNAFQRWQYVWJF-UHFFFAOYSA-N 4-[[1-[2-bis[4-(dimethylamino)-3,5-dimethylphenyl]phosphanylnaphthalen-1-yl]naphthalen-2-yl]-[4-(dimethylamino)-3,5-dimethylphenyl]phosphanyl]-n,n,2,6-tetramethylaniline Chemical group C1=C(C)C(N(C)C)=C(C)C=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=C(C)C(N(C)C)=C(C)C=1)C=1C=C(C)C(N(C)C)=C(C)C=1)C1=CC(C)=C(N(C)C)C(C)=C1 KXNAFQRWQYVWJF-UHFFFAOYSA-N 0.000 description 1
• NOLMSXJJRKOIOF-UHFFFAOYSA-N 4-bis(4-tert-butylphenyl)phosphanylpentan-2-yl-bis(4-tert-butylphenyl)phosphane Chemical compound C=1C=C(C(C)(C)C)C=CC=1P(C=1C=CC(=CC=1)C(C)(C)C)C(C)CC(C)P(C=1C=CC(=CC=1)C(C)(C)C)C1=CC=C(C(C)(C)C)C=C1 NOLMSXJJRKOIOF-UHFFFAOYSA-N 0.000 description 1
• OHMDCKMTIZTPKB-UHFFFAOYSA-N 4-methyl-1,1-dinaphthalen-1-ylpentane-1,2-diamine Chemical compound C1=CC=C2C(C(N)(C=3C4=CC=CC=C4C=CC=3)C(N)CC(C)C)=CC=CC2=C1 OHMDCKMTIZTPKB-UHFFFAOYSA-N 0.000 description 1
• PEXFGZJGEXXSBE-UHFFFAOYSA-N 4-methyl-1,1-diphenylpentane-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)(C(N)CC(C)C)C1=CC=CC=C1 PEXFGZJGEXXSBE-UHFFFAOYSA-N 0.000 description 1
• 125000003119 4-methyl-3-pentenyl group Chemical group [H]\C(=C(/C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• OXUOPBPAVLQNGC-UHFFFAOYSA-N 422509-53-3 Chemical compound O1C=2C=CC3=CC=CC=C3C=2C(C2=CC=CC=C2C=C2)=C2OP1NC(C)C1=CC=CC=C1 OXUOPBPAVLQNGC-UHFFFAOYSA-N 0.000 description 1
• OHGGHRJGBXAKKY-UHFFFAOYSA-N 490023-37-5 Chemical compound O1C=2C=CC3=CC=CC=C3C=2C(C2=CC=CC=C2C=C2)=C2OP1N(C)CC1=CC=CC=C1 OHGGHRJGBXAKKY-UHFFFAOYSA-N 0.000 description 1
• BGFRWTOLXXYTIQ-UHFFFAOYSA-N 5-chloro-4-(trifluoromethyl)pyridin-2-amine;hydrochloride Chemical compound Cl.NC1=CC(C(F)(F)F)=C(Cl)C=N1 BGFRWTOLXXYTIQ-UHFFFAOYSA-N 0.000 description 1
• 125000006043 5-hexenyl group Chemical group 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
• KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• GSAWZQFVBUKOLE-PUHLOBNQSA-N C1(=C(C=C(N=C1)NC(=O)C=1SC(=NC=1)/C(=N/C(C1=CC=C(OC)C=C1)C1=CC=C(OC)C=C1)/C)C(F)(F)F)Cl Chemical compound C1(=C(C=C(N=C1)NC(=O)C=1SC(=NC=1)/C(=N/C(C1=CC=C(OC)C=C1)C1=CC=C(OC)C=C1)/C)C(F)(F)F)Cl GSAWZQFVBUKOLE-PUHLOBNQSA-N 0.000 description 1
• KIBPGQHLUKJTSK-WGOQTCKBSA-N C1(=CC=C(C=C1)C(F)(F)F)/C(=N/C(C1=CC=CC=C1)C1=CC=CC=C1)/C Chemical compound C1(=CC=C(C=C1)C(F)(F)F)/C(=N/C(C1=CC=CC=C1)C1=CC=CC=C1)/C KIBPGQHLUKJTSK-WGOQTCKBSA-N 0.000 description 1
• QJAUGPBCUJLPEZ-OQKWZONESA-N C1(=CC=CC=C1)C(/N=C(\C)/C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C(/N=C(\C)/C1=CC=CC=C1)C1=CC=CC=C1 QJAUGPBCUJLPEZ-OQKWZONESA-N 0.000 description 1
• VFYDQLUPXAVOIK-UHFFFAOYSA-N C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C(=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1)C(CN)N.[Fe+2] Chemical compound C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C(=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1)C(CN)N.[Fe+2] VFYDQLUPXAVOIK-UHFFFAOYSA-N 0.000 description 1
• 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 description 1
• MLAJMVOVWHUBJB-NSKAYECMSA-N C1=C(C(=CC(=N1)NC(=O)C=1SC(=NC=1)/C(=N/C1=CC=C(C=C1)OC)/C)C(F)(F)F)Cl Chemical compound C1=C(C(=CC(=N1)NC(=O)C=1SC(=NC=1)/C(=N/C1=CC=C(C=C1)OC)/C)C(F)(F)F)Cl MLAJMVOVWHUBJB-NSKAYECMSA-N 0.000 description 1
• ZYUZLEUJKZZXNN-UHFFFAOYSA-N C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 Chemical group C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 ZYUZLEUJKZZXNN-UHFFFAOYSA-N 0.000 description 1
• 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 description 1
• SSUFDOMYCBCHML-UHFFFAOYSA-N CCCCC[S](=O)=O Chemical group CCCCC[S](=O)=O SSUFDOMYCBCHML-UHFFFAOYSA-N 0.000 description 1
• VFJAGQKSXVVSSJ-UHFFFAOYSA-N CCc1cc(CC)cc(c1)P(c1cc(CC)cc(CC)c1)c1ccc2ccccc2c1-c1c(ccc2ccccc12)P(c1cc(CC)cc(CC)c1)c1cc(CC)cc(CC)c1 Chemical group CCc1cc(CC)cc(c1)P(c1cc(CC)cc(CC)c1)c1ccc2ccccc2c1-c1c(ccc2ccccc12)P(c1cc(CC)cc(CC)c1)c1cc(CC)cc(CC)c1 VFJAGQKSXVVSSJ-UHFFFAOYSA-N 0.000 description 1
• NOLMSXJJRKOIOF-CZNDPXEESA-N C[C@H](C[C@@H](C)P(C1=CC=C(C=C1)C(C)(C)C)C1=CC=C(C=C1)C(C)(C)C)P(C1=CC=C(C=C1)C(C)(C)C)C1=CC=C(C=C1)C(C)(C)C Chemical compound C[C@H](C[C@@H](C)P(C1=CC=C(C=C1)C(C)(C)C)C1=CC=C(C=C1)C(C)(C)C)P(C1=CC=C(C=C1)C(C)(C)C)C1=CC=C(C=C1)C(C)(C)C NOLMSXJJRKOIOF-CZNDPXEESA-N 0.000 description 1
• ULBXWWGWDPVHAO-UHFFFAOYSA-N Chlorbufam Chemical compound C#CC(C)OC(=O)NC1=CC=CC(Cl)=C1 ULBXWWGWDPVHAO-UHFFFAOYSA-N 0.000 description 1
• PABGPKPBPXOJDF-OPEKNORGSA-N ClC=1C(=CC(=NC=1)NC(=O)C1=CN=C(S1)/C(/C)=N/CC1=CC=C(C=C1)OC)C(F)(F)F Chemical compound ClC=1C(=CC(=NC=1)NC(=O)C1=CN=C(S1)/C(/C)=N/CC1=CC=C(C=C1)OC)C(F)(F)F PABGPKPBPXOJDF-OPEKNORGSA-N 0.000 description 1
• 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
• 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
• 102100023578 Cyclic AMP-dependent transcription factor ATF-7 Human genes 0.000 description 1
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
• XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• 101000905723 Homo sapiens Cyclic AMP-dependent transcription factor ATF-7 Proteins 0.000 description 1
• 101000610640 Homo sapiens U4/U6 small nuclear ribonucleoprotein Prp3 Proteins 0.000 description 1
• ACIMRXKJKQGBGL-UHFFFAOYSA-N N-(2-aminoethyl)-5-chloro-1-naphthalenesulfonamide Chemical compound C1=CC=C2C(S(=O)(=O)NCCN)=CC=CC2=C1Cl ACIMRXKJKQGBGL-UHFFFAOYSA-N 0.000 description 1
• GLHYBSXRZULGGH-UHFFFAOYSA-N N-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-2-[1-[(2,4-dimethoxyphenyl)methylamino]ethyl]-1,3-thiazole-5-carboxamide Chemical compound C1(=C(C=C(N=C1)NC(=O)C1=CN=C(S1)C(C)NCC1=CC=C(OC)C=C1OC)C(F)(F)F)Cl GLHYBSXRZULGGH-UHFFFAOYSA-N 0.000 description 1
• JYHLGSFKJQSNFK-UHFFFAOYSA-N N-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-2-[1-[(4-methoxyphenyl)methylamino]ethyl]-1,3-thiazole-5-carboxamide Chemical compound ClC=1C(=CC(=NC=1)NC(=O)C1=CN=C(S1)C(C)NCC1=CC=C(C=C1)OC)C(F)(F)F JYHLGSFKJQSNFK-UHFFFAOYSA-N 0.000 description 1
• FBERCSMWGGTWCI-UHFFFAOYSA-N N-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-2-[N-[(2,4-dimethoxyphenyl)methyl]-C-methylcarbonimidoyl]-1,3-thiazole-5-carboxamide Chemical compound ClC=1C(=CC(=NC=1)NC(=O)C1=CN=C(S1)C(C)=NCC1=C(C=C(C=C1)OC)OC)C(F)(F)F FBERCSMWGGTWCI-UHFFFAOYSA-N 0.000 description 1
• PABGPKPBPXOJDF-UHFFFAOYSA-N N-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-2-[N-[(4-methoxyphenyl)methyl]-C-methylcarbonimidoyl]-1,3-thiazole-5-carboxamide Chemical compound ClC=1C(=CC(=NC=1)NC(=O)C1=CN=C(S1)C(C)=NCC1=CC=C(C=C1)OC)C(F)(F)F PABGPKPBPXOJDF-UHFFFAOYSA-N 0.000 description 1
• 206010028980 Neoplasm Diseases 0.000 description 1
• LDPFQXCGMQVRHW-HMMYKYKNSA-N O1C(=CC=C1)\C(\C)=N\C(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound O1C(=CC=C1)\C(\C)=N\C(C1=CC=CC=C1)C1=CC=CC=C1 LDPFQXCGMQVRHW-HMMYKYKNSA-N 0.000 description 1
• 101150003085 Pdcl gene Proteins 0.000 description 1
• 108010066684 Proto-Oncogene Proteins A-raf Proteins 0.000 description 1
• 101001110823 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-A Proteins 0.000 description 1
• 101000712176 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-B Proteins 0.000 description 1
• 229910018286 SbF 6 Inorganic materials 0.000 description 1
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
• GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
• 102100040374 U4/U6 small nuclear ribonucleoprotein Prp3 Human genes 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
• QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
• CDJHPMXMJUCLPA-YRNSEASESA-N [(2r,3r)-3-diphenylphosphanyl-2-bicyclo[2.2.1]hept-5-enyl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P([C@H]1[C@@H](C2C=CC1C2)P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 CDJHPMXMJUCLPA-YRNSEASESA-N 0.000 description 1
• CTYPJIUQROQJBG-JWQCQUIFSA-N [(2r,4r)-4-diphenylphosphanylpentan-2-yl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P([C@H](C)C[C@@H](C)P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 CTYPJIUQROQJBG-JWQCQUIFSA-N 0.000 description 1
• XLWCIHPMASUXPI-ZDUSSCGKSA-N [(2s)-1-phenylpropan-2-yl]benzene Chemical compound C([C@H](C)C=1C=CC=CC=1)C1=CC=CC=C1 XLWCIHPMASUXPI-ZDUSSCGKSA-N 0.000 description 1
• CTYPJIUQROQJBG-DQEYMECFSA-N [(2s,4s)-4-diphenylphosphanylpentan-2-yl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P([C@@H](C)C[C@H](C)P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 CTYPJIUQROQJBG-DQEYMECFSA-N 0.000 description 1
• GYKMEKRMASHMIH-VSJLXWSYSA-N [(3r,4r)-1-benzyl-4-diphenylphosphanylpyrrolidin-3-yl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P([C@H]1[C@@H](CN(C1)CC=1C=CC=CC=1)P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 GYKMEKRMASHMIH-VSJLXWSYSA-N 0.000 description 1
• IXQOLSZPQCIXEX-UHFFFAOYSA-N [1-(2-diphenylphosphanyl-6-methylnaphthalen-1-yl)-6-methylnaphthalen-2-yl]-diphenylphosphane Chemical group C1=CC2=CC(C)=CC=C2C(C=2C3=CC=C(C)C=C3C=CC=2P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 IXQOLSZPQCIXEX-UHFFFAOYSA-N 0.000 description 1
• YEKBVMDAGDTOQB-UHFFFAOYSA-L [1-(2-diphenylphosphanylnaphthalen-1-yl)naphthalen-2-yl]-diphenylphosphane;ruthenium(2+);dichloride Chemical compound Cl[Ru]Cl.C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 YEKBVMDAGDTOQB-UHFFFAOYSA-L 0.000 description 1
• KRWTWSSMURUMDE-UHFFFAOYSA-N [1-(2-methoxynaphthalen-1-yl)naphthalen-2-yl]-diphenylphosphane Chemical group COC1=CC=C2C=CC=CC2=C1C(C1=CC=CC=C1C=C1)=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 KRWTWSSMURUMDE-UHFFFAOYSA-N 0.000 description 1
• CRELPJJGSLSRBO-UHFFFAOYSA-N [1-[2-bis(3,5-ditert-butyl-4-methoxyphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(3,5-ditert-butyl-4-methoxyphenyl)phosphane Chemical group C1=C(C(C)(C)C)C(OC)=C(C(C)(C)C)C=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=C(C(OC)=C(C=1)C(C)(C)C)C(C)(C)C)C=1C=C(C(OC)=C(C=1)C(C)(C)C)C(C)(C)C)C1=CC(C(C)(C)C)=C(OC)C(C(C)(C)C)=C1 CRELPJJGSLSRBO-UHFFFAOYSA-N 0.000 description 1
• CFGHBQVJUPCBQC-UHFFFAOYSA-N [1-[2-bis(3,5-ditert-butylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(3,5-ditert-butylphenyl)phosphane Chemical group CC(C)(C)C1=CC(C(C)(C)C)=CC(P(C=2C=C(C=C(C=2)C(C)(C)C)C(C)(C)C)C=2C(=C3C=CC=CC3=CC=2)C=2C3=CC=CC=C3C=CC=2P(C=2C=C(C=C(C=2)C(C)(C)C)C(C)(C)C)C=2C=C(C=C(C=2)C(C)(C)C)C(C)(C)C)=C1 CFGHBQVJUPCBQC-UHFFFAOYSA-N 0.000 description 1
• MKSPFBHJYJGYHW-UHFFFAOYSA-N [1-[2-bis(4-methoxy-3,5-dimethylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(4-methoxy-3,5-dimethylphenyl)phosphane Chemical group C1=C(C)C(OC)=C(C)C=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=C(C)C(OC)=C(C)C=1)C=1C=C(C)C(OC)=C(C)C=1)C1=CC(C)=C(OC)C(C)=C1 MKSPFBHJYJGYHW-UHFFFAOYSA-N 0.000 description 1
• IOPQYDKQISFMJI-UHFFFAOYSA-N [1-[2-bis(4-methylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(4-methylphenyl)phosphane Chemical group C1=CC(C)=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 IOPQYDKQISFMJI-UHFFFAOYSA-N 0.000 description 1
• YYGPOCGVEZBYHP-UHFFFAOYSA-N [1-[2-bis(4-pyrrolidin-1-ylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(4-pyrrolidin-1-ylphenyl)phosphane Chemical group C1CCCN1C1=CC=C(P(C=2C=CC(=CC=2)N2CCCC2)C=2C(=C3C=CC=CC3=CC=2)C=2C3=CC=CC=C3C=CC=2P(C=2C=CC(=CC=2)N2CCCC2)C=2C=CC(=CC=2)N2CCCC2)C=C1 YYGPOCGVEZBYHP-UHFFFAOYSA-N 0.000 description 1
• GDKBCRWEMVZCJU-UHFFFAOYSA-N [1-[2-bis[3,5-di(propan-2-yl)phenyl]phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis[3,5-di(propan-2-yl)phenyl]phosphane Chemical group CC(C)C1=CC(C(C)C)=CC(P(C=2C=C(C=C(C=2)C(C)C)C(C)C)C=2C(=C3C=CC=CC3=CC=2)C=2C3=CC=CC=C3C=CC=2P(C=2C=C(C=C(C=2)C(C)C)C(C)C)C=2C=C(C=C(C=2)C(C)C)C(C)C)=C1 GDKBCRWEMVZCJU-UHFFFAOYSA-N 0.000 description 1
• KRJVQCZJJSUHHO-UHFFFAOYSA-N [2-(2-diphenylphosphanyl-6-methoxyphenyl)-3-methoxyphenyl]-diphenylphosphane Chemical group COC=1C=CC=C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1C=1C(OC)=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 KRJVQCZJJSUHHO-UHFFFAOYSA-N 0.000 description 1
• KSYUVEBIHJNKIE-UHFFFAOYSA-N [8-(7-diphenylphosphanyl-4-methyl-2,3-dihydro-1,4-benzoxazin-8-yl)-4-methyl-2,3-dihydro-1,4-benzoxazin-7-yl]-diphenylphosphane Chemical compound CN1CCOC(C=2C=3C(=CC=C4N(C)CCOC4=3)P(C=3C=CC=CC=3)C=3C=CC=CC=3)=C1C=CC=2P(C=1C=CC=CC=1)C1=CC=CC=C1 KSYUVEBIHJNKIE-UHFFFAOYSA-N 0.000 description 1
• HBQDCKPPSIWZLY-UHFFFAOYSA-M [dimethylamino-(2-oxopyridin-1-yl)oxymethylidene]-dimethylazanium;trifluoroborane;fluoride Chemical compound [F-].FB(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O HBQDCKPPSIWZLY-UHFFFAOYSA-M 0.000 description 1
• CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
• 125000006323 alkenyl amino group Chemical group 0.000 description 1
• 125000005108 alkenylthio group Chemical group 0.000 description 1
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 1
• 125000005130 alkyl carbonyl thio group Chemical group 0.000 description 1
• 125000005103 alkyl silyl group Chemical group 0.000 description 1
• 125000005153 alkyl sulfamoyl group Chemical group 0.000 description 1
• 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
• 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
• 125000000304 alkynyl group Chemical group 0.000 description 1
• 125000005336 allyloxy group Chemical group 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
• 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
• 239000012300 argon atmosphere Substances 0.000 description 1
• 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 1
• 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 description 1
• 125000004659 aryl alkyl thio group Chemical group 0.000 description 1
• 125000005135 aryl sulfinyl group Chemical group 0.000 description 1
• 125000005110 aryl thio group Chemical group 0.000 description 1
• YCNIBOIOWCTRCL-UHFFFAOYSA-N azane;2,2,2-trifluoroacetic acid Chemical compound [NH4+].[O-]C(=O)C(F)(F)F YCNIBOIOWCTRCL-UHFFFAOYSA-N 0.000 description 1
• JTGLIMITPXICFA-UHFFFAOYSA-N azanium;2-oxo-1h-pyridine-3-carboxylate Chemical compound [NH4+].[O-]C(=O)C1=CC=CNC1=O JTGLIMITPXICFA-UHFFFAOYSA-N 0.000 description 1
• DYVKGOVCCLREIY-UHFFFAOYSA-N azanium;pyridine-2-carboxylate Chemical compound [NH4+].[O-]C(=O)C1=CC=CC=N1 DYVKGOVCCLREIY-UHFFFAOYSA-N 0.000 description 1
• 125000002393 azetidinyl group Chemical group 0.000 description 1
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
• 125000004069 aziridinyl group Chemical group 0.000 description 1
• 159000000009 barium salts Chemical class 0.000 description 1
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
• 235000019445 benzyl alcohol Nutrition 0.000 description 1
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
• YHNUDLCUIKMNSN-UHFFFAOYSA-N bis(1,2,4-triazol-1-yl)methanone Chemical compound C1=NC=NN1C(=O)N1C=NC=N1 YHNUDLCUIKMNSN-UHFFFAOYSA-N 0.000 description 1
• HROGQYMZWGPHIB-UHFFFAOYSA-N bis(4-methoxyphenyl)methanamine Chemical compound C1=CC(OC)=CC=C1C(N)C1=CC=C(OC)C=C1 HROGQYMZWGPHIB-UHFFFAOYSA-N 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 150000001638 boron Chemical class 0.000 description 1
• 229910052796 boron Inorganic materials 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 229910052794 bromium Inorganic materials 0.000 description 1
• QVYARBLCAHCSFJ-UHFFFAOYSA-N butane-1,1-diamine Chemical compound CCCC(N)N QVYARBLCAHCSFJ-UHFFFAOYSA-N 0.000 description 1
• 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
• 159000000007 calcium salts Chemical class 0.000 description 1
• 201000011510 cancer Diseases 0.000 description 1
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
• 230000003197 catalytic effect Effects 0.000 description 1
• 238000006555 catalytic reaction Methods 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 238000006757 chemical reactions by type Methods 0.000 description 1
• FWXAUDSWDBGCMN-ZEQRLZLVSA-N chiraphos Chemical compound C=1C=CC=CC=1P([C@@H](C)[C@H](C)P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 FWXAUDSWDBGCMN-ZEQRLZLVSA-N 0.000 description 1
• 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
• OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
• 125000006310 cycloalkyl amino group Chemical group 0.000 description 1
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 description 1
• 125000000753 cycloalkyl group Chemical group 0.000 description 1
• 125000005366 cycloalkylthio group Chemical group 0.000 description 1
• 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
• DBBUVLSRTWYISN-UHFFFAOYSA-N cycloheptane-1,2-diamine Chemical compound NC1CCCCCC1N DBBUVLSRTWYISN-UHFFFAOYSA-N 0.000 description 1
• 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
• SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
• NKLCHDQGUHMCGL-UHFFFAOYSA-N cyclohexylidenemethanone Chemical group O=C=C1CCCCC1 NKLCHDQGUHMCGL-UHFFFAOYSA-N 0.000 description 1
• 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
• HOXDXGRSZJEEKN-UHFFFAOYSA-N cycloocta-1,5-diene;rhodium Chemical class [Rh].C1CC=CCCC=C1 HOXDXGRSZJEEKN-UHFFFAOYSA-N 0.000 description 1
• 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
• 125000004410 cyclooctyloxy group Chemical group C1(CCCCCCC1)O* 0.000 description 1
• 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
• 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
• 230000018044 dehydration Effects 0.000 description 1
• 238000006297 dehydration reaction Methods 0.000 description 1
• OKKJLVBELUTLKV-MICDWDOJSA-N deuteriomethanol Chemical compound [2H]CO OKKJLVBELUTLKV-MICDWDOJSA-N 0.000 description 1
• 229910052805 deuterium Inorganic materials 0.000 description 1
• UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
• DPOGTJDEMBEUSH-UHFFFAOYSA-N dicyclohexyl(ethyl)phosphane Chemical compound C1CCCCC1P(CC)C1CCCCC1 DPOGTJDEMBEUSH-UHFFFAOYSA-N 0.000 description 1
• SKCMIKXIHUVXEG-UHFFFAOYSA-N dicyclohexyl-[2-(2-dicyclohexylphosphanyl-6-methylphenyl)-3-methylphenyl]phosphane Chemical group CC=1C=CC=C(P(C2CCCCC2)C2CCCCC2)C=1C=1C(C)=CC=CC=1P(C1CCCCC1)C1CCCCC1 SKCMIKXIHUVXEG-UHFFFAOYSA-N 0.000 description 1
• AJDPNPAGZMZOMN-UHFFFAOYSA-N diethyl (4-oxo-1,2,3-benzotriazin-3-yl) phosphate Chemical compound C1=CC=C2C(=O)N(OP(=O)(OCC)OCC)N=NC2=C1 AJDPNPAGZMZOMN-UHFFFAOYSA-N 0.000 description 1
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
• 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 description 1
• 125000005435 dihydrobenzoxazolyl group Chemical group O1C(NC2=C1C=CC=C2)* 0.000 description 1
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
• OUQSAXROROGQEE-UHFFFAOYSA-N diphenyl-[2-(4-propan-2-yl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]phosphane Chemical compound CC(C)C1COC(C=2C(=CC=CC=2)P(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 OUQSAXROROGQEE-UHFFFAOYSA-N 0.000 description 1
• 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 238000004821 distillation Methods 0.000 description 1
• 239000012153 distilled water Substances 0.000 description 1
• ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
• VJYFKVYYMZPMAB-UHFFFAOYSA-N ethoprophos Chemical compound CCCSP(=O)(OCC)SCCC VJYFKVYYMZPMAB-UHFFFAOYSA-N 0.000 description 1
• HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 229910052731 fluorine Inorganic materials 0.000 description 1
• 125000004612 furopyridinyl group Chemical group O1C(=CC2=C1C=CC=N2)* 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 150000002258 gallium Chemical class 0.000 description 1
• 150000004820 halides Chemical class 0.000 description 1
• 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000004468 heterocyclylthio group Chemical group 0.000 description 1
• 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
• 125000002632 imidazolidinyl group Chemical group 0.000 description 1
• 125000002636 imidazolinyl group Chemical group 0.000 description 1
• 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 239000011261 inert gas Substances 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 125000002346 iodo group Chemical group I* 0.000 description 1
• 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
• 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
• 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
• 125000005956 isoquinolyl group Chemical group 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• 125000000842 isoxazolyl group Chemical group 0.000 description 1
• 229940043355 kinase inhibitor Drugs 0.000 description 1
• 159000000003 magnesium salts Chemical class 0.000 description 1
• FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
• SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 1
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 150000004682 monohydrates Chemical class 0.000 description 1
• OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 description 1
• LQVZUXUQGFIYEK-UHFFFAOYSA-N n-methyloxolan-3-amine Chemical compound CNC1CCOC1 LQVZUXUQGFIYEK-UHFFFAOYSA-N 0.000 description 1
• 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
• 125000000627 niacin group Chemical group 0.000 description 1
• 235000001968 nicotinic acid Nutrition 0.000 description 1
• 239000011664 nicotinic acid Substances 0.000 description 1
• 229960003512 nicotinic acid Drugs 0.000 description 1
• 239000012044 organic layer Substances 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 125000003566 oxetanyl group Chemical group 0.000 description 1
• 230000001590 oxidative effect Effects 0.000 description 1
• 238000006146 oximation reaction Methods 0.000 description 1
• 125000000466 oxiranyl group Chemical group 0.000 description 1
• BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
• PBDBXAQKXCXZCJ-UHFFFAOYSA-L palladium(2+);2,2,2-trifluoroacetate Chemical compound [Pd+2].[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F PBDBXAQKXCXZCJ-UHFFFAOYSA-L 0.000 description 1
• LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
• 125000002097 pentamethylcyclopentadienyl group Chemical group 0.000 description 1
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
• 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
• 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
• 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
• 125000005954 phenoxathiinyl group Chemical group 0.000 description 1
• 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
• 125000004344 phenylpropyl group Chemical group 0.000 description 1
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
• UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
• FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
• GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
• 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
• GGHDAUPFEBTORZ-UHFFFAOYSA-N propane-1,1-diamine Chemical compound CCC(N)N GGHDAUPFEBTORZ-UHFFFAOYSA-N 0.000 description 1
• 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
• 239000003909 protein kinase inhibitor Substances 0.000 description 1
• 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
• 125000003226 pyrazolyl group Chemical group 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• 125000004076 pyridyl group Chemical group 0.000 description 1
• 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 description 1
• 125000000714 pyrimidinyl group Chemical group 0.000 description 1
• 125000001422 pyrrolinyl group Chemical group 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
• 229910052703 rhodium Inorganic materials 0.000 description 1
• 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
• 239000000741 silica gel Substances 0.000 description 1
• 229910002027 silica gel Inorganic materials 0.000 description 1
• 159000000000 sodium salts Chemical class 0.000 description 1
• 239000012453 solvate Substances 0.000 description 1
• 238000001228 spectrum Methods 0.000 description 1
• 125000003003 spiro group Chemical group 0.000 description 1
• 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 1
• KIVOUBJXVKDUOF-UHFFFAOYSA-N tert-butyl N-[1-[5-[[5-chloro-4-(trifluoromethyl)pyridin-2-yl]carbamoyl]-1,3-thiazol-2-yl]ethylideneamino]carbamate Chemical compound ClC=1C(=CC(=NC=1)NC(=O)C1=CN=C(S1)C(C)=NNC(=O)OC(C)(C)C)C(F)(F)F KIVOUBJXVKDUOF-UHFFFAOYSA-N 0.000 description 1
• DYZXXFQARICWBZ-QMMMGPOBSA-N tert-butyl N-[[(1S)-1-[5-[[5-chloro-4-(trifluoromethyl)pyridin-2-yl]carbamoyl]-1,3-thiazol-2-yl]ethyl]amino]carbamate Chemical compound C1(=C(C=C(N=C1)NC(=O)C1=CN=C(S1)[C@H](C)NNC(=O)OC(C)(C)C)C(F)(F)F)Cl DYZXXFQARICWBZ-QMMMGPOBSA-N 0.000 description 1
• DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
• 125000006337 tetrafluoro ethyl group Chemical group 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
• CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• 229940126585 therapeutic drug Drugs 0.000 description 1
• GGNIKGLUPSHSBV-UHFFFAOYSA-N thiazole-5-carboxamide Chemical compound NC(=O)C1=CN=CS1 GGNIKGLUPSHSBV-UHFFFAOYSA-N 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• 125000002053 thietanyl group Chemical group 0.000 description 1
• 125000001730 thiiranyl group Chemical group 0.000 description 1
• 125000004149 thio group Chemical group *S* 0.000 description 1
• 125000004306 triazinyl group Chemical group 0.000 description 1
• 125000001425 triazolyl group Chemical group 0.000 description 1
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
• WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
• BTJRYMWSJCKXIN-GWQXNCQPSA-N trihydroxy-[(3S)-2'-phenylspiro[1,2-dihydroindene-3,3'-2,5-dihydro-1H-indene]-4'-ylidene]-lambda5-phosphane Chemical compound C1C[C@]2(C(CC3=C2C(=P(O)(O)O)CC=C3)C4=CC=CC=C4)C5=CC=CC=C51 BTJRYMWSJCKXIN-GWQXNCQPSA-N 0.000 description 1
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000005500 uronium group Chemical group 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 150000003754 zirconium Chemical class 0.000 description 1
• 229910052726 zirconium Inorganic materials 0.000 description 1
• 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1