JP2007508305A - ピラゾロピリジンおよびその類似物 - Google Patents

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Publication number

JP2007508305A

JP2007508305A JP2006534174A JP2006534174A JP2007508305A JP 2007508305 A JP2007508305 A JP 2007508305A JP 2006534174 A JP2006534174 A JP 2006534174A JP 2006534174 A JP2006534174 A JP 2006534174A JP 2007508305 A JP2007508305 A JP 2007508305A

Authority

JP

Japan

Prior art keywords

group

alkyl

alkylenyl

amino

aryl

Prior art date

2003-10-03

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Withdrawn

Links

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• AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 271
• 238000000034 method Methods 0.000 claims abstract description 63
• 102000004127 Cytokines Human genes 0.000 claims abstract description 33
• 108090000695 Cytokines Proteins 0.000 claims abstract description 33
• 241001465754 Metazoa Species 0.000 claims abstract description 28
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 28
• 201000010099 disease Diseases 0.000 claims abstract description 26
• 230000015572 biosynthetic process Effects 0.000 claims abstract description 22
• 230000001613 neoplastic effect Effects 0.000 claims abstract description 9
• 230000003612 virological effect Effects 0.000 claims abstract description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
• -1 nitro, hydroxy Chemical group 0.000 claims description 544
• 125000000217 alkyl group Chemical group 0.000 claims description 371
• 125000005466 alkylenyl group Chemical group 0.000 claims description 264
• 125000003118 aryl group Chemical group 0.000 claims description 222
• 125000001072 heteroaryl group Chemical group 0.000 claims description 215
• 239000001257 hydrogen Substances 0.000 claims description 200
• 229910052739 hydrogen Inorganic materials 0.000 claims description 200
• 125000000623 heterocyclic group Chemical group 0.000 claims description 196
• 125000002947 alkylene group Chemical group 0.000 claims description 159
• 150000002431 hydrogen Chemical group 0.000 claims description 159
• 150000003839 salts Chemical class 0.000 claims description 157
• 125000003342 alkenyl group Chemical group 0.000 claims description 107
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 96
• 125000000304 alkynyl group Chemical group 0.000 claims description 92
• 125000001424 substituent group Chemical group 0.000 claims description 87
• 125000003545 alkoxy group Chemical group 0.000 claims description 83
• 229910052736 halogen Inorganic materials 0.000 claims description 79
• 125000000732 arylene group Chemical group 0.000 claims description 71
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 61
• 150000002367 halogens Chemical group 0.000 claims description 61
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 60
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 60
• 125000001188 haloalkyl group Chemical group 0.000 claims description 59
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 54
• 125000005549 heteroarylene group Chemical group 0.000 claims description 51
• 125000004450 alkenylene group Chemical group 0.000 claims description 49
• 125000004419 alkynylene group Chemical group 0.000 claims description 48
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 48
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 46
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 46
• 125000004104 aryloxy group Chemical group 0.000 claims description 44
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 41
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 35
• 125000005843 halogen group Chemical group 0.000 claims description 33
• 125000005842 heteroatom Chemical group 0.000 claims description 33
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 31
• 125000003282 alkyl amino group Chemical group 0.000 claims description 30
• 125000004414 alkyl thio group Chemical group 0.000 claims description 29
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 29
• 229910052757 nitrogen Inorganic materials 0.000 claims description 28
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
• 229920006395 saturated elastomer Polymers 0.000 claims description 27
• 125000005532 aryl alkyleneoxy group Chemical group 0.000 claims description 26
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 25
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 25
• 125000005529 alkyleneoxy group Chemical group 0.000 claims description 23
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 22
• 229910052717 sulfur Inorganic materials 0.000 claims description 22
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
• ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 20
• 230000002452 interceptive effect Effects 0.000 claims description 18
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
• 125000001153 fluoro group Chemical group F* 0.000 claims description 13
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 11
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
• LJCJRRKKAKAKRV-UHFFFAOYSA-N (2-amino-2-methylpropyl) 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical group CC(C)(N)COC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 LJCJRRKKAKAKRV-UHFFFAOYSA-N 0.000 claims description 10
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 10
• 125000002256 xylenyl group Chemical group C1(C(C=CC=C1)C)(C)* 0.000 claims description 10
• SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims description 9
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 9
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 8
• 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 claims description 8
• 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 claims description 7
• 230000001939 inductive effect Effects 0.000 claims description 7
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 10
• 125000001769 aryl amino group Chemical group 0.000 claims 3
• 150000001555 benzenes Chemical group 0.000 claims 2
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
• 239000000543 intermediate Substances 0.000 abstract description 7
• 239000002955 immunomodulating agent Substances 0.000 abstract description 2
• 229940121354 immunomodulator Drugs 0.000 abstract description 2
• ZSSQCBFDXFPYMW-UHFFFAOYSA-N 6,7,8,9-tetrahydro-5h-pyrazolo[3,4-h]quinolin-4-amine Chemical compound N1NCC2=C1CCC1=C2N=CC=C1N ZSSQCBFDXFPYMW-UHFFFAOYSA-N 0.000 abstract 1
• QHEKSRCAJJJQEH-UHFFFAOYSA-N C1=CC2=C(N)C=CNC2=C2C=NN=C21 Chemical compound C1=CC2=C(N)C=CNC2=C2C=NN=C21 QHEKSRCAJJJQEH-UHFFFAOYSA-N 0.000 abstract 1
• AYOFVXCHEISMTL-UHFFFAOYSA-N pyrazolo[4,3-b][1,8]naphthyridin-4-amine Chemical compound C1=CN=C2N(N)C3=CN=NC3=CC2=C1 AYOFVXCHEISMTL-UHFFFAOYSA-N 0.000 abstract 1
• QKBAHVJPUXNRJC-UHFFFAOYSA-N pyrazolo[4,3-b]pyridin-4-amine Chemical compound NN1C=CC=C2N=NC=C12 QKBAHVJPUXNRJC-UHFFFAOYSA-N 0.000 abstract 1
• 238000006243 chemical reaction Methods 0.000 description 327
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 101
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
• 239000002904 solvent Substances 0.000 description 82
• 239000000047 product Substances 0.000 description 81
• 238000007796 conventional method Methods 0.000 description 80
• 239000000243 solution Substances 0.000 description 76
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 72
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 63
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 56
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 47
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
• 239000000203 mixture Substances 0.000 description 45
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 44
• LONFHWIJSLLRRX-UHFFFAOYSA-N 3h-pyrazolo[3,4-c]quinoline Chemical compound C1=CC=C2C3=CNN=C3C=NC2=C1 LONFHWIJSLLRRX-UHFFFAOYSA-N 0.000 description 43
• 230000002829 reductive effect Effects 0.000 description 39
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
• 239000007787 solid Substances 0.000 description 32
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 26
• 125000004043 oxo group Chemical group O=* 0.000 description 26
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 24
• 239000013078 crystal Substances 0.000 description 24
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 24
• 238000001914 filtration Methods 0.000 description 23
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
• 230000008018 melting Effects 0.000 description 22
• 238000002844 melting Methods 0.000 description 22
• 229910000029 sodium carbonate Inorganic materials 0.000 description 22
• 229960000583 acetic acid Drugs 0.000 description 21
• 238000004458 analytical method Methods 0.000 description 21
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
• 239000002585 base Substances 0.000 description 20
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 20
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 20
• 238000010992 reflux Methods 0.000 description 20
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 19
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
• 239000003153 chemical reaction reagent Substances 0.000 description 19
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
• 239000000908 ammonium hydroxide Substances 0.000 description 18
• 238000004587 chromatography analysis Methods 0.000 description 17
• 150000002576 ketones Chemical class 0.000 description 16
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 16
• 235000019341 magnesium sulphate Nutrition 0.000 description 16
• 239000003921 oil Substances 0.000 description 16
• 235000019198 oils Nutrition 0.000 description 16
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 15
• KOPFEFZSAMLEHK-UHFFFAOYSA-M 1h-pyrazole-5-carboxylate Chemical compound [O-]C(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-M 0.000 description 14
• MGLHICIVLQDMID-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-pyrazolo[3,4-c]quinoline Chemical compound C1=CC=CC2=C3CNNC3CN=C21 MGLHICIVLQDMID-UHFFFAOYSA-N 0.000 description 14
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 14
• 150000001412 amines Chemical class 0.000 description 14
• 238000010438 heat treatment Methods 0.000 description 14
• 239000000463 material Substances 0.000 description 14
• 238000010189 synthetic method Methods 0.000 description 14
• YMJLEPMVGQBLHL-UHFFFAOYSA-N 1h-pyrazole-5-carbonitrile Chemical compound N#CC1=CC=NN1 YMJLEPMVGQBLHL-UHFFFAOYSA-N 0.000 description 13
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 13
• 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 13
• 238000005859 coupling reaction Methods 0.000 description 13
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 239000000460 chlorine Substances 0.000 description 12
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
• 239000002244 precipitate Substances 0.000 description 12
• BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical compound NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 description 11
• FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical class C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 11
• 230000002378 acidificating effect Effects 0.000 description 11
• 238000007792 addition Methods 0.000 description 11
• LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 11
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 11
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 10
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 10
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
• 229910052794 bromium Inorganic materials 0.000 description 10
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
• 239000012299 nitrogen atmosphere Substances 0.000 description 10
• 235000011056 potassium acetate Nutrition 0.000 description 10
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
• 125000003396 thiol group Chemical class [H]S* 0.000 description 10
• MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 9
• 241000700605 Viruses Species 0.000 description 9
• 150000001408 amides Chemical class 0.000 description 9
• 125000003277 amino group Chemical group 0.000 description 9
• 239000000284 extract Substances 0.000 description 9
• 230000028993 immune response Effects 0.000 description 9
• 239000010410 layer Substances 0.000 description 9
• 230000004048 modification Effects 0.000 description 9
• 238000012986 modification Methods 0.000 description 9
• 150000001299 aldehydes Chemical class 0.000 description 8
• 150000001350 alkyl halides Chemical class 0.000 description 8
• 125000004432 carbon atom Chemical group C* 0.000 description 8
• 238000004519 manufacturing process Methods 0.000 description 8
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
• 238000000746 purification Methods 0.000 description 8
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
• WPDASZCYRKGSTO-UHFFFAOYSA-N (2-aminophenyl)boronic acid;hydrochloride Chemical compound Cl.NC1=CC=CC=C1B(O)O WPDASZCYRKGSTO-UHFFFAOYSA-N 0.000 description 7
• 206010028980 Neoplasm Diseases 0.000 description 7
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
• 125000004122 cyclic group Chemical group 0.000 description 7
• 238000010511 deprotection reaction Methods 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
• 125000006239 protecting group Chemical group 0.000 description 7
• 229910052938 sodium sulfate Inorganic materials 0.000 description 7
• 235000011152 sodium sulphate Nutrition 0.000 description 7
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical group ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 7
• 229910052723 transition metal Inorganic materials 0.000 description 7
• 150000003624 transition metals Chemical group 0.000 description 7
• 238000010626 work up procedure Methods 0.000 description 7
• 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 6
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 6
• 235000019502 Orange oil Nutrition 0.000 description 6
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 6
• 239000012346 acetyl chloride Substances 0.000 description 6
• 150000008064 anhydrides Chemical class 0.000 description 6
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
• 230000008878 coupling Effects 0.000 description 6
• 238000010168 coupling process Methods 0.000 description 6
• 150000002148 esters Chemical class 0.000 description 6
• 239000000706 filtrate Substances 0.000 description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
• 239000012948 isocyanate Substances 0.000 description 6
• 150000002513 isocyanates Chemical class 0.000 description 6
• 150000002825 nitriles Chemical group 0.000 description 6
• 239000010502 orange oil Substances 0.000 description 6
• 229910000027 potassium carbonate Inorganic materials 0.000 description 6
• 159000000000 sodium salts Chemical class 0.000 description 6
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
• 239000007858 starting material Substances 0.000 description 6
• NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 6
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• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
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