NO20022847L - Nye substituerte tricykliske forbindelser - Google Patents

Info

Publication number

NO20022847L

NO20022847L NO20022847A NO20022847A NO20022847L NO 20022847 L NO20022847 L NO 20022847L NO 20022847 A NO20022847 A NO 20022847A NO 20022847 A NO20022847 A NO 20022847A NO 20022847 L NO20022847 L NO 20022847L

Authority

NO

Norway

Prior art keywords

group

atom

compound

lower alkyl

general formula

Prior art date

1999-12-16

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• 150000001875 compounds Chemical class 0.000 title claims description 407
• 238000000034 method Methods 0.000 claims description 117
• 125000000217 alkyl group Chemical group 0.000 claims description 91
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 80
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 74
• 238000002360 preparation method Methods 0.000 claims description 69
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 60
• 125000002252 acyl group Chemical group 0.000 claims description 45
• 125000006242 amine protecting group Chemical group 0.000 claims description 40
• 125000005843 halogen group Chemical group 0.000 claims description 39
• 150000003839 salts Chemical class 0.000 claims description 39
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
• 229910052801 chlorine Inorganic materials 0.000 claims description 23
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
• 229910052757 nitrogen Inorganic materials 0.000 claims description 18
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
• 229910052717 sulfur Inorganic materials 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 17
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 17
• 125000004434 sulfur atom Chemical group 0.000 claims description 17
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
• 239000003814 drug Substances 0.000 claims description 15
• 125000006239 protecting group Chemical group 0.000 claims description 15
• 125000004432 carbon atom Chemical group C* 0.000 claims description 13
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
• 229940079593 drug Drugs 0.000 claims description 12
• 239000003513 alkali Substances 0.000 claims description 11
• 229910052731 fluorine Inorganic materials 0.000 claims description 11
• 206010012601 diabetes mellitus Diseases 0.000 claims description 10
• 208000008589 Obesity Diseases 0.000 claims description 8
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 8
• 125000001153 fluoro group Chemical group F* 0.000 claims description 8
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 8
• 235000020824 obesity Nutrition 0.000 claims description 8
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 7
• NUDXTWXBZSGOFS-UHFFFAOYSA-N 2-[[7-(trifluoromethyl)-9h-carbazol-2-yl]oxy]ethanamine Chemical compound FC(F)(F)C1=CC=C2C3=CC=C(OCCN)C=C3NC2=C1 NUDXTWXBZSGOFS-UHFFFAOYSA-N 0.000 claims description 3
• OEYXNGHJHLGQRD-UHFFFAOYSA-N n-[3-[1-hydroxy-2-[2-[(7-hydroxy-9h-carbazol-2-yl)oxy]ethylamino]ethyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C(O)CNCCOC=2C=C3C(C4=CC=C(O)C=C4N3)=CC=2)=C1 OEYXNGHJHLGQRD-UHFFFAOYSA-N 0.000 claims description 3
• NKBJHYNSIOMSRB-QHCPKHFHSA-N n-[2-bromo-5-[(1r)-1-hydroxy-2-[2-[(7-hydroxy-9h-carbazol-2-yl)oxy]ethylamino]ethyl]phenyl]methanesulfonamide Chemical compound C1=C(Br)C(NS(=O)(=O)C)=CC([C@@H](O)CNCCOC=2C=C3C(C4=CC=C(O)C=C4N3)=CC=2)=C1 NKBJHYNSIOMSRB-QHCPKHFHSA-N 0.000 claims description 2
• NKBJHYNSIOMSRB-HSZRJFAPSA-N n-[2-bromo-5-[(1s)-1-hydroxy-2-[2-[(7-hydroxy-9h-carbazol-2-yl)oxy]ethylamino]ethyl]phenyl]methanesulfonamide Chemical compound C1=C(Br)C(NS(=O)(=O)C)=CC([C@H](O)CNCCOC=2C=C3C(C4=CC=C(O)C=C4N3)=CC=2)=C1 NKBJHYNSIOMSRB-HSZRJFAPSA-N 0.000 claims description 2
• NKBJHYNSIOMSRB-UHFFFAOYSA-N n-[2-bromo-5-[1-hydroxy-2-[2-[(7-hydroxy-9h-carbazol-2-yl)oxy]ethylamino]ethyl]phenyl]methanesulfonamide Chemical compound C1=C(Br)C(NS(=O)(=O)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC=C(O)C=C4N3)=CC=2)=C1 NKBJHYNSIOMSRB-UHFFFAOYSA-N 0.000 claims description 2
• CVTDCZZWSTUEGR-QHCPKHFHSA-N n-[2-chloro-5-[(1r)-1-hydroxy-2-[2-[(7-hydroxy-9h-carbazol-2-yl)oxy]ethylamino]ethyl]phenyl]methanesulfonamide Chemical compound C1=C(Cl)C(NS(=O)(=O)C)=CC([C@@H](O)CNCCOC=2C=C3C(C4=CC=C(O)C=C4N3)=CC=2)=C1 CVTDCZZWSTUEGR-QHCPKHFHSA-N 0.000 claims description 2
• CVTDCZZWSTUEGR-HSZRJFAPSA-N n-[2-chloro-5-[(1s)-1-hydroxy-2-[2-[(7-hydroxy-9h-carbazol-2-yl)oxy]ethylamino]ethyl]phenyl]methanesulfonamide Chemical compound C1=C(Cl)C(NS(=O)(=O)C)=CC([C@H](O)CNCCOC=2C=C3C(C4=CC=C(O)C=C4N3)=CC=2)=C1 CVTDCZZWSTUEGR-HSZRJFAPSA-N 0.000 claims description 2
• CVTDCZZWSTUEGR-UHFFFAOYSA-N n-[2-chloro-5-[1-hydroxy-2-[2-[(7-hydroxy-9h-carbazol-2-yl)oxy]ethylamino]ethyl]phenyl]methanesulfonamide Chemical compound C1=C(Cl)C(NS(=O)(=O)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC=C(O)C=C4N3)=CC=2)=C1 CVTDCZZWSTUEGR-UHFFFAOYSA-N 0.000 claims description 2
• YVYJNOCMDYTZHC-HSZRJFAPSA-N n-[2-hydroxy-5-[(1s)-1-hydroxy-2-[2-[(7-hydroxy-9h-carbazol-2-yl)oxy]ethylamino]ethyl]phenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC([C@H](O)CNCCOC=2C=C3C(C4=CC=C(O)C=C4N3)=CC=2)=C1 YVYJNOCMDYTZHC-HSZRJFAPSA-N 0.000 claims description 2
• YVYJNOCMDYTZHC-UHFFFAOYSA-N n-[2-hydroxy-5-[1-hydroxy-2-[2-[(7-hydroxy-9h-carbazol-2-yl)oxy]ethylamino]ethyl]phenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC=C(O)C=C4N3)=CC=2)=C1 YVYJNOCMDYTZHC-UHFFFAOYSA-N 0.000 claims description 2
• OEYXNGHJHLGQRD-QHCPKHFHSA-N n-[3-[(1r)-1-hydroxy-2-[2-[(7-hydroxy-9h-carbazol-2-yl)oxy]ethylamino]ethyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC([C@@H](O)CNCCOC=2C=C3C(C4=CC=C(O)C=C4N3)=CC=2)=C1 OEYXNGHJHLGQRD-QHCPKHFHSA-N 0.000 claims description 2
• NLGKUIQGKNFPGB-QHCPKHFHSA-N n-[3-[(1r)-2-[2-[(7-amino-9h-carbazol-2-yl)oxy]ethylamino]-1-hydroxyethyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC([C@@H](O)CNCCOC=2C=C3C(C4=CC=C(N)C=C4N3)=CC=2)=C1 NLGKUIQGKNFPGB-QHCPKHFHSA-N 0.000 claims description 2
• OEYXNGHJHLGQRD-HSZRJFAPSA-N n-[3-[(1s)-1-hydroxy-2-[2-[(7-hydroxy-9h-carbazol-2-yl)oxy]ethylamino]ethyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC([C@H](O)CNCCOC=2C=C3C(C4=CC=C(O)C=C4N3)=CC=2)=C1 OEYXNGHJHLGQRD-HSZRJFAPSA-N 0.000 claims description 2
• ZVMQYJHQKYAFBJ-QHCPKHFHSA-N n-[5-[(1r)-2-[2-[(7-amino-9h-carbazol-2-yl)oxy]ethylamino]-1-hydroxyethyl]-2-chlorophenyl]methanesulfonamide Chemical compound C1=C(Cl)C(NS(=O)(=O)C)=CC([C@@H](O)CNCCOC=2C=C3C(C4=CC=C(N)C=C4N3)=CC=2)=C1 ZVMQYJHQKYAFBJ-QHCPKHFHSA-N 0.000 claims description 2
• SDXHUJXCZWOCOP-VWLOTQADSA-N n-[7-[2-[[(2r)-2-[4-chloro-3-(methanesulfonamido)phenyl]-2-hydroxyethyl]amino]ethoxy]-9h-carbazol-2-yl]acetamide Chemical compound C1([C@@H](O)CNCCOC=2C=C3NC=4C(C3=CC=2)=CC=C(C=4)NC(=O)C)=CC=C(Cl)C(NS(C)(=O)=O)=C1 SDXHUJXCZWOCOP-VWLOTQADSA-N 0.000 claims description 2
• ATCTYSBPKNGGSX-VWLOTQADSA-N n-[7-[2-[[(2r)-2-hydroxy-2-[3-(methanesulfonamido)phenyl]ethyl]amino]ethoxy]-9h-carbazol-2-yl]acetamide Chemical compound C1([C@@H](O)CNCCOC=2C=C3NC=4C(C3=CC=2)=CC=C(C=4)NC(=O)C)=CC=CC(NS(C)(=O)=O)=C1 ATCTYSBPKNGGSX-VWLOTQADSA-N 0.000 claims description 2
• OSKYOLRWQQFDJD-UHFFFAOYSA-N 2-[(7-bromo-9h-carbazol-2-yl)oxy]ethanamine Chemical compound BrC1=CC=C2C3=CC=C(OCCN)C=C3NC2=C1 OSKYOLRWQQFDJD-UHFFFAOYSA-N 0.000 claims 1
• SDODUNPMQAELTD-UHFFFAOYSA-N 2-[(7-chloro-9h-carbazol-2-yl)oxy]ethanamine Chemical compound ClC1=CC=C2C3=CC=C(OCCN)C=C3NC2=C1 SDODUNPMQAELTD-UHFFFAOYSA-N 0.000 claims 1
• IBZYSADYXSENEN-UHFFFAOYSA-N 2-[(7-fluoro-9h-carbazol-2-yl)oxy]ethanamine Chemical compound FC1=CC=C2C3=CC=C(OCCN)C=C3NC2=C1 IBZYSADYXSENEN-UHFFFAOYSA-N 0.000 claims 1
• AKINSSYKOZEBHE-UHFFFAOYSA-N 2-[(7-methoxy-9h-carbazol-2-yl)oxy]ethanamine Chemical compound NCCOC1=CC=C2C3=CC=C(OC)C=C3NC2=C1 AKINSSYKOZEBHE-UHFFFAOYSA-N 0.000 claims 1
• LALXZBPJUBYWSV-UHFFFAOYSA-N 2-[(7-methyl-9h-carbazol-2-yl)oxy]ethanamine Chemical compound NCCOC1=CC=C2C3=CC=C(C)C=C3NC2=C1 LALXZBPJUBYWSV-UHFFFAOYSA-N 0.000 claims 1
• TYQSCRWFSQPOGZ-UHFFFAOYSA-N 2-[(7-phenylmethoxy-9h-carbazol-2-yl)oxy]ethanamine Chemical compound C=1C(OCCN)=CC=C(C2=CC=3)C=1NC2=CC=3OCC1=CC=CC=C1 TYQSCRWFSQPOGZ-UHFFFAOYSA-N 0.000 claims 1
• APVNJAFWVJRPSG-UHFFFAOYSA-N 7-[2-(benzylamino)ethoxy]-9h-carbazole-2-carbonitrile Chemical compound C=1C(C#N)=CC=C(C2=CC=3)C=1NC2=CC=3OCCNCC1=CC=CC=C1 APVNJAFWVJRPSG-UHFFFAOYSA-N 0.000 claims 1
• 239000004480 active ingredient Substances 0.000 claims 1
• AYTZXLMDPDLVQT-UHFFFAOYSA-N n-[7-(2-aminoethoxy)-9h-carbazol-2-yl]acetamide Chemical compound NCCOC1=CC=C2C3=CC=C(NC(=O)C)C=C3NC2=C1 AYTZXLMDPDLVQT-UHFFFAOYSA-N 0.000 claims 1
• FVOMBQKGVBWDED-UHFFFAOYSA-N n-[7-[2-(benzylamino)ethoxy]-9h-carbazol-2-yl]acetamide Chemical compound C=1C(NC(=O)C)=CC=C(C2=CC=3)C=1NC2=CC=3OCCNCC1=CC=CC=C1 FVOMBQKGVBWDED-UHFFFAOYSA-N 0.000 claims 1
• ICNISNQNYVEZDW-UHFFFAOYSA-N n-benzyl-2-[(7-bromo-9h-carbazol-2-yl)oxy]ethanamine Chemical compound C=1C(Br)=CC=C(C2=CC=3)C=1NC2=CC=3OCCNCC1=CC=CC=C1 ICNISNQNYVEZDW-UHFFFAOYSA-N 0.000 claims 1
• UFDGKKVNFSBBPQ-UHFFFAOYSA-N n-benzyl-2-[(7-chloro-9h-carbazol-2-yl)oxy]ethanamine Chemical compound C=1C(Cl)=CC=C(C2=CC=3)C=1NC2=CC=3OCCNCC1=CC=CC=C1 UFDGKKVNFSBBPQ-UHFFFAOYSA-N 0.000 claims 1
• RIPWPDZKYGLBTE-UHFFFAOYSA-N n-benzyl-2-[(7-fluoro-9h-carbazol-2-yl)oxy]ethanamine Chemical compound C=1C(F)=CC=C(C2=CC=3)C=1NC2=CC=3OCCNCC1=CC=CC=C1 RIPWPDZKYGLBTE-UHFFFAOYSA-N 0.000 claims 1
• MUMMMTXNPPHGFH-UHFFFAOYSA-N n-benzyl-2-[(7-methoxy-9h-carbazol-2-yl)oxy]ethanamine Chemical compound C=1C(OC)=CC=C(C2=CC=3)C=1NC2=CC=3OCCNCC1=CC=CC=C1 MUMMMTXNPPHGFH-UHFFFAOYSA-N 0.000 claims 1
• VRWSSDYFXVCKCG-UHFFFAOYSA-N n-benzyl-2-[(7-methyl-9h-carbazol-2-yl)oxy]ethanamine Chemical compound C=1C(C)=CC=C(C2=CC=3)C=1NC2=CC=3OCCNCC1=CC=CC=C1 VRWSSDYFXVCKCG-UHFFFAOYSA-N 0.000 claims 1
• UYRJIBCKEFXJSR-UHFFFAOYSA-N n-benzyl-2-[(7-phenylmethoxy-9h-carbazol-2-yl)oxy]ethanamine Chemical compound C=1C=CC=CC=1CNCCOC(C=1)=CC=C(C2=CC=3)C=1NC2=CC=3OCC1=CC=CC=C1 UYRJIBCKEFXJSR-UHFFFAOYSA-N 0.000 claims 1
• HQQMEGKVBWZOLP-UHFFFAOYSA-N n-benzyl-2-[[7-(trifluoromethyl)-9h-carbazol-2-yl]oxy]ethanamine Chemical compound C=1C(C(F)(F)F)=CC=C(C2=CC=3)C=1NC2=CC=3OCCNCC1=CC=CC=C1 HQQMEGKVBWZOLP-UHFFFAOYSA-N 0.000 claims 1
• 230000002265 prevention Effects 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 198
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 129
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 96
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 62
• 238000006243 chemical reaction Methods 0.000 description 57
• 239000000543 intermediate Substances 0.000 description 57
• 239000000203 mixture Substances 0.000 description 57
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 52
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
• 239000002904 solvent Substances 0.000 description 51
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
• 238000005160 1H NMR spectroscopy Methods 0.000 description 44
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 35
• 239000000243 solution Substances 0.000 description 32
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
• 239000012295 chemical reaction liquid Substances 0.000 description 25
• 230000000694 effects Effects 0.000 description 24
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
• 239000002253 acid Substances 0.000 description 20
• 238000010898 silica gel chromatography Methods 0.000 description 20
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
• 239000012044 organic layer Substances 0.000 description 16
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 15
• 239000000126 substance Substances 0.000 description 15
• 125000001424 substituent group Chemical group 0.000 description 15
• 239000000460 chlorine Substances 0.000 description 13
• -1 isobutyryl Chemical group 0.000 description 13
• 239000012046 mixed solvent Substances 0.000 description 13
• NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 13
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
• 229910000027 potassium carbonate Inorganic materials 0.000 description 12
• 239000002516 radical scavenger Substances 0.000 description 12
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
• 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 12
• 229910052740 iodine Inorganic materials 0.000 description 11
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 10
• 239000000556 agonist Substances 0.000 description 10
• 239000012300 argon atmosphere Substances 0.000 description 10
• 239000003054 catalyst Substances 0.000 description 10
• 108090000623 proteins and genes Proteins 0.000 description 10
• 238000006722 reduction reaction Methods 0.000 description 10
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
• 241000699666 Mus <mouse, genus> Species 0.000 description 9
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
• 150000001412 amines Chemical class 0.000 description 9
• 238000004519 manufacturing process Methods 0.000 description 9
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
• 239000011541 reaction mixture Substances 0.000 description 9
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 8
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
• 229910052794 bromium Inorganic materials 0.000 description 8
• 201000010099 disease Diseases 0.000 description 8
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
• 239000000706 filtrate Substances 0.000 description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
• 238000010992 reflux Methods 0.000 description 8
• 238000012360 testing method Methods 0.000 description 8
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
• 230000003287 optical effect Effects 0.000 description 7
• 230000009467 reduction Effects 0.000 description 7
• 229910052721 tungsten Inorganic materials 0.000 description 7
• 230000007306 turnover Effects 0.000 description 7
• 229910052727 yttrium Inorganic materials 0.000 description 7
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
• 229910052786 argon Inorganic materials 0.000 description 6
• UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 6
• 239000003638 chemical reducing agent Substances 0.000 description 6
• 238000007796 conventional method Methods 0.000 description 6
• 238000001816 cooling Methods 0.000 description 6
• 239000012043 crude product Substances 0.000 description 6
• 239000013078 crystal Substances 0.000 description 6
• 238000001914 filtration Methods 0.000 description 6
• 239000013067 intermediate product Substances 0.000 description 6
• 239000010410 layer Substances 0.000 description 6
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