SK150297A3 - Alpha-substituted pyrimidine-thioalkyl and alkylether compounds as inhibitors of viral reverse transcriptase - Google Patents

Info

Publication number

SK150297A3

SK150297A3 SK1502-97A SK150297A SK150297A3 SK 150297 A3 SK150297 A3 SK 150297A3 SK 150297 A SK150297 A SK 150297A SK 150297 A3 SK150297 A3 SK 150297A3

Authority

SK

Slovakia

Prior art keywords

dihydro

pyridinyl

amino

chloro

compound

Prior art date

1995-05-08

Links

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• -1 alkylether compounds Chemical class 0.000 title claims abstract description 535
• 102100034343 Integrase Human genes 0.000 title abstract description 10
• 108010092799 RNA-directed DNA polymerase Proteins 0.000 title abstract description 10
• 230000003612 virological effect Effects 0.000 title abstract description 9
• 239000003112 inhibitor Substances 0.000 title abstract description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 449
• 125000001475 halogen functional group Chemical group 0.000 claims abstract 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 260
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 128
• 229910052757 nitrogen Inorganic materials 0.000 claims description 70
• 238000000034 method Methods 0.000 claims description 54
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 53
• 229910052739 hydrogen Inorganic materials 0.000 claims description 47
• HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 claims description 47
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 42
• 229910052736 halogen Inorganic materials 0.000 claims description 37
• 239000001257 hydrogen Substances 0.000 claims description 37
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 31
• 229920006395 saturated elastomer Polymers 0.000 claims description 30
• 208000030507 AIDS Diseases 0.000 claims description 27
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
• 229910052799 carbon Inorganic materials 0.000 claims description 25
• 150000002367 halogens Chemical class 0.000 claims description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• 241000725303 Human immunodeficiency virus Species 0.000 claims description 20
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 20
• 150000002431 hydrogen Chemical class 0.000 claims description 19
• 125000001544 thienyl group Chemical group 0.000 claims description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
• 239000000460 chlorine Substances 0.000 claims description 13
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
• 150000003839 salts Chemical class 0.000 claims description 12
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 11
• 125000005843 halogen group Chemical group 0.000 claims description 11
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
• 125000001624 naphthyl group Chemical group 0.000 claims description 10
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 10
• 125000000217 alkyl group Chemical group 0.000 claims description 8
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
• 125000004193 piperazinyl group Chemical group 0.000 claims description 7
• 150000001204 N-oxides Chemical class 0.000 claims description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 5
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 5
• DLUPKDAJXDJCTN-UHFFFAOYSA-N 6-chloro-2-(1-isoquinolin-3-ylethylsulfanyl)pyrimidin-4-amine Chemical compound C=1C2=CC=CC=C2C=NC=1C(C)SC1=NC(N)=CC(Cl)=N1 DLUPKDAJXDJCTN-UHFFFAOYSA-N 0.000 claims description 5
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 150000004677 hydrates Chemical class 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 239000012453 solvate Substances 0.000 claims description 5
• 125000004434 sulfur atom Chemical group 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
• 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 4
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 4
• 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 4
• 125000004534 benzothien-2-yl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 4
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 4
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 claims description 4
• 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 3
• 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims description 3
• NRTBNQSBXMHVGW-ONEGZZNKSA-N (e)-4-(4-amino-6-chloropyrimidin-2-yl)sulfanyl-1-pyrrolidin-1-ylbut-2-en-1-one Chemical compound NC1=CC(Cl)=NC(SC\C=C\C(=O)N2CCCC2)=N1 NRTBNQSBXMHVGW-ONEGZZNKSA-N 0.000 claims description 3
• SMEXPIBTHBJCLQ-SNAWJCMRSA-N (e)-4-(4-amino-6-chloropyrimidin-2-yl)sulfanyl-n-ethyl-n-methylbut-2-enamide Chemical compound CCN(C)C(=O)\C=C\CSC1=NC(N)=CC(Cl)=N1 SMEXPIBTHBJCLQ-SNAWJCMRSA-N 0.000 claims description 3
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
• FTPLHCPJZLDACP-UHFFFAOYSA-N 5,6-dihydrofuro[2,3-d]pyrimidine Chemical compound N1=CN=C2OCCC2=C1 FTPLHCPJZLDACP-UHFFFAOYSA-N 0.000 claims description 3
• BCCIPSPVTGITDC-UHFFFAOYSA-N 5,6-dihydrothieno[2,3-d]pyrimidine Chemical compound N1=CN=C2SCCC2=C1 BCCIPSPVTGITDC-UHFFFAOYSA-N 0.000 claims description 3
• MJDXSLDHQYJHAT-UHFFFAOYSA-N 5-bromo-6-chloro-2-(1-isoquinolin-3-ylethylsulfanyl)pyrimidin-4-amine Chemical compound C=1C2=CC=CC=C2C=NC=1C(C)SC1=NC(N)=C(Br)C(Cl)=N1 MJDXSLDHQYJHAT-UHFFFAOYSA-N 0.000 claims description 3
• PANGDCFLXUDHDI-UHFFFAOYSA-N 6,7-dihydro-5h-pyrrolo[2,3-d]pyrimidine Chemical compound N1=CN=C2NCCC2=C1 PANGDCFLXUDHDI-UHFFFAOYSA-N 0.000 claims description 3
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 3
• JJTNLWSCFYERCK-UHFFFAOYSA-N 7h-pyrrolo[2,3-d]pyrimidine Chemical compound N1=CN=C2NC=CC2=C1 JJTNLWSCFYERCK-UHFFFAOYSA-N 0.000 claims description 3
• 241000700605 Viruses Species 0.000 claims description 3
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
• KQGXYVJZOMKLSA-UHFFFAOYSA-N furo[2,3-d]pyrimidine Chemical compound N1=CN=C2OC=CC2=C1 KQGXYVJZOMKLSA-UHFFFAOYSA-N 0.000 claims description 3
• 125000001041 indolyl group Chemical group 0.000 claims description 3
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
• CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 claims description 3
• UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 claims description 3
• JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 3
• DDWBRNXDKNIQDY-UHFFFAOYSA-N thieno[2,3-d]pyrimidine Chemical compound N1=CN=C2SC=CC2=C1 DDWBRNXDKNIQDY-UHFFFAOYSA-N 0.000 claims description 3
• 239000000427 antigen Substances 0.000 claims description 2
• 102000036639 antigens Human genes 0.000 claims description 2
• 108091007433 antigens Proteins 0.000 claims description 2
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 5
• UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 claims 3
• RYAYFARBZXVJPF-UHFFFAOYSA-N 6-amino-2-(naphthalen-2-ylmethylsulfanyl)pyrimidine-4-carbonitrile Chemical compound NC1=CC(C#N)=NC(SCC=2C=C3C=CC=CC3=CC=2)=N1 RYAYFARBZXVJPF-UHFFFAOYSA-N 0.000 claims 2
• 125000004615 furo[2,3-b]pyridinyl group Chemical group O1C(=CC=2C1=NC=CC2)* 0.000 claims 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 claims 2
• WSYFORMNOZEAEJ-AATRIKPKSA-N (e)-4-(4-amino-6-chloropyrimidin-2-yl)sulfanyl-n,n-diethylbut-2-enamide Chemical compound CCN(CC)C(=O)\C=C\CSC1=NC(N)=CC(Cl)=N1 WSYFORMNOZEAEJ-AATRIKPKSA-N 0.000 claims 1
• FOEMIZSFFWGXHX-UHFFFAOYSA-N 2-methylsulfanylpyrimidine Chemical compound CSC1=NC=CC=N1 FOEMIZSFFWGXHX-UHFFFAOYSA-N 0.000 claims 1
• 206010061598 Immunodeficiency Diseases 0.000 claims 1
• 208000029462 Immunodeficiency disease Diseases 0.000 claims 1
• PFRUBEOIWWEFOL-UHFFFAOYSA-N [N].[S] Chemical group [N].[S] PFRUBEOIWWEFOL-UHFFFAOYSA-N 0.000 claims 1
• 230000007813 immunodeficiency Effects 0.000 claims 1
• 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 claims 1
• DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 claims 1
• 150000005215 alkyl ethers Chemical class 0.000 abstract description 6
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 461
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 441
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 404
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 270
• 239000000243 solution Substances 0.000 description 206
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 201
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 168
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 160
• 229940093499 ethyl acetate Drugs 0.000 description 153
• 235000019439 ethyl acetate Nutrition 0.000 description 153
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 149
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 142
• 239000000741 silica gel Substances 0.000 description 141
• 229910002027 silica gel Inorganic materials 0.000 description 141
• 239000011541 reaction mixture Substances 0.000 description 140
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 136
• 238000005160 1H NMR spectroscopy Methods 0.000 description 101
• 239000000203 mixture Substances 0.000 description 84
• CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 81
• 239000003921 oil Substances 0.000 description 78
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 74
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 74
• 238000001819 mass spectrum Methods 0.000 description 73
• 229910000027 potassium carbonate Inorganic materials 0.000 description 71
• 235000011181 potassium carbonates Nutrition 0.000 description 71
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 68
• 239000007787 solid Substances 0.000 description 63
• 238000002360 preparation method Methods 0.000 description 60
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 52
• 239000002480 mineral oil Substances 0.000 description 52
• 235000010446 mineral oil Nutrition 0.000 description 52
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 51
• 238000004809 thin layer chromatography Methods 0.000 description 51
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
• 238000006243 chemical reaction Methods 0.000 description 50
• 239000013058 crude material Substances 0.000 description 48
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 46
• 239000010410 layer Substances 0.000 description 45
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 44
• 229910000104 sodium hydride Inorganic materials 0.000 description 43
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 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 38
• 239000000284 extract Substances 0.000 description 38
• 238000010992 reflux Methods 0.000 description 36
• IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 31
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 30
• 239000012312 sodium hydride Substances 0.000 description 30
• 239000000706 filtrate Substances 0.000 description 28
• 125000001424 substituent group Chemical group 0.000 description 28
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 26
• FXUDMQXADIQKFJ-UHFFFAOYSA-N 4-amino-6-chloro-1h-pyrimidine-2-thione Chemical compound NC1=CC(Cl)=NC(S)=N1 FXUDMQXADIQKFJ-UHFFFAOYSA-N 0.000 description 21
• OITKEKZIJXHOMS-UHFFFAOYSA-N 4-amino-6-chloro-1h-pyrimidine-2-thione;methanesulfonic acid Chemical compound CS(O)(=O)=O.NC1=CC(Cl)=NC(S)=N1 OITKEKZIJXHOMS-UHFFFAOYSA-N 0.000 description 20
• 238000002844 melting Methods 0.000 description 19
• 230000008018 melting Effects 0.000 description 19
• 239000012141 concentrate Substances 0.000 description 18
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 18
• 235000019341 magnesium sulphate Nutrition 0.000 description 18
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
• 238000004458 analytical method Methods 0.000 description 17
• 239000012065 filter cake Substances 0.000 description 17
• 238000003756 stirring Methods 0.000 description 17
• 238000004587 chromatography analysis Methods 0.000 description 16
• 239000000725 suspension Substances 0.000 description 15
• 238000005804 alkylation reaction Methods 0.000 description 14
• 239000012267 brine Substances 0.000 description 14
• 238000002425 crystallisation Methods 0.000 description 14
• 230000008025 crystallization Effects 0.000 description 14
• 239000006185 dispersion Substances 0.000 description 14
• 229910052938 sodium sulfate Inorganic materials 0.000 description 14
• 235000011152 sodium sulphate Nutrition 0.000 description 14
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
• 230000029936 alkylation Effects 0.000 description 13
• 150000001721 carbon Chemical group 0.000 description 13
• 239000006260 foam Substances 0.000 description 13
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 12
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 12
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 11
• 238000010791 quenching Methods 0.000 description 11
• 239000003039 volatile agent Substances 0.000 description 11
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 10
• 102000004190 Enzymes Human genes 0.000 description 10
• 108090000790 Enzymes Proteins 0.000 description 10
• 238000005481 NMR spectroscopy Methods 0.000 description 10
• 239000000908 ammonium hydroxide Substances 0.000 description 10
• 238000001816 cooling Methods 0.000 description 10
• 229940088598 enzyme Drugs 0.000 description 10
• NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 10
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 10
• 239000012044 organic layer Substances 0.000 description 10
• 239000000126 substance Substances 0.000 description 10
• BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 9
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 9
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
• IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
• JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 8
• NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 8
• 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 7
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