SK4032001A3 - Novel substituted indolinones with an inhibitory effect on various kinases and cyclin/cdk complexes - Google Patents

Info

Publication number

SK4032001A3

SK4032001A3 SK403-2001A SK4032001A SK4032001A3 SK 4032001 A3 SK4032001 A3 SK 4032001A3 SK 4032001 A SK4032001 A SK 4032001A SK 4032001 A3 SK4032001 A3 SK 4032001A3

Authority

SK

Slovakia

Prior art keywords

alkyl

substituted

amino

group

alkylamino

Prior art date

1998-09-25

Links

• Espacenet
• Global Dossier
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• JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 title claims abstract description 26
• 102000016736 Cyclin Human genes 0.000 title abstract description 9
• 108050006400 Cyclin Proteins 0.000 title abstract description 9
• 230000002401 inhibitory effect Effects 0.000 title abstract description 4
• 108091000080 Phosphotransferase Proteins 0.000 title description 4
• 102000020233 phosphotransferase Human genes 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 342
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 254
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 45
• 150000003839 salts Chemical class 0.000 claims abstract description 30
• 229940002612 prodrug Drugs 0.000 claims abstract description 4
• 239000000651 prodrug Substances 0.000 claims abstract description 4
• -1 carboxy- Chemical class 0.000 claims description 757
• 229910052757 nitrogen Inorganic materials 0.000 claims description 297
• 229910052739 hydrogen Inorganic materials 0.000 claims description 263
• 125000000217 alkyl group Chemical group 0.000 claims description 91
• 239000000460 chlorine Substances 0.000 claims description 60
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 45
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 42
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 39
• 229910052801 chlorine Inorganic materials 0.000 claims description 39
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
• 229910052794 bromium Inorganic materials 0.000 claims description 29
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 27
• 229910052731 fluorine Inorganic materials 0.000 claims description 27
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 26
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
• 239000011737 fluorine Substances 0.000 claims description 19
• 238000006243 chemical reaction Methods 0.000 claims description 18
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
• 239000001257 hydrogen Substances 0.000 claims description 17
• 229910052740 iodine Inorganic materials 0.000 claims description 17
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
• 125000003277 amino group Chemical group 0.000 claims description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 15
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 14
• 125000001624 naphthyl group Chemical group 0.000 claims description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 125000003282 alkyl amino group Chemical group 0.000 claims description 13
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
• 125000001424 substituent group Chemical group 0.000 claims description 12
• 238000006467 substitution reaction Methods 0.000 claims description 12
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
• 238000000034 method Methods 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 150000001412 amines Chemical class 0.000 claims description 10
• 125000005122 aminoalkylamino group Chemical group 0.000 claims description 10
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
• 125000003118 aryl group Chemical group 0.000 claims description 8
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
• 125000001153 fluoro group Chemical group F* 0.000 claims description 8
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
• 150000002148 esters Chemical class 0.000 claims description 7
• 125000006239 protecting group Chemical group 0.000 claims description 7
• 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 6
• 125000006842 cycloalkyleneimino group Chemical group 0.000 claims description 6
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
• 125000005544 phthalimido group Chemical group 0.000 claims description 6
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• 238000002360 preparation method Methods 0.000 claims description 6
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 5
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
• 230000010933 acylation Effects 0.000 claims description 5
• 238000005917 acylation reaction Methods 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 5
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 5
• 150000003951 lactams Chemical group 0.000 claims description 5
• 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
• 239000002243 precursor Chemical group 0.000 claims description 5
• 239000007790 solid phase Chemical group 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
• 230000029936 alkylation Effects 0.000 claims description 4
• 238000005804 alkylation reaction Methods 0.000 claims description 4
• 239000000969 carrier Substances 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 230000032050 esterification Effects 0.000 claims description 4
• 238000005886 esterification reaction Methods 0.000 claims description 4
• 125000005241 heteroarylamino group Chemical group 0.000 claims description 4
• 239000000126 substance Substances 0.000 claims description 4
• 125000004434 sulfur atom Chemical group 0.000 claims description 4
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
• YZQYLXVWTQKHNY-QPLCGJKRSA-N (3z)-3-[[4-(2-morpholin-4-ylethyl)anilino]-phenylmethylidene]-5-nitro-1h-indol-2-one Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)\C1=C(C=1C=CC=CC=1)/NC(C=C1)=CC=C1CCN1CCOCC1 YZQYLXVWTQKHNY-QPLCGJKRSA-N 0.000 claims description 3
• HNCRQCVXZXSJRP-FCQUAONHSA-N (3z)-3-[[4-[(dimethylamino)methyl]anilino]-phenylmethylidene]-5-nitro-1h-indol-2-one Chemical compound C1=CC(CN(C)C)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC([N+]([O-])=O)=CC=C2NC\1=O HNCRQCVXZXSJRP-FCQUAONHSA-N 0.000 claims description 3
• JUXFRGURUWQIRC-VHXPQNKSSA-N (3z)-3-[[4-[2-(dimethylamino)ethyl]anilino]-phenylmethylidene]-5-nitro-1h-indol-2-one Chemical compound C1=CC(CCN(C)C)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC([N+]([O-])=O)=CC=C2NC\1=O JUXFRGURUWQIRC-VHXPQNKSSA-N 0.000 claims description 3
• 125000006602 (C1-C3) alkylsulfonylamino group Chemical group 0.000 claims description 3
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
• 230000009435 amidation Effects 0.000 claims description 3
• 238000007112 amidation reaction Methods 0.000 claims description 3
• 230000004663 cell proliferation Effects 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims description 3
• 230000007062 hydrolysis Effects 0.000 claims description 3
• 238000006460 hydrolysis reaction Methods 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 125000006525 methoxy ethyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])OC([H])([H])[H] 0.000 claims description 3
• SGVAUCIEUYKEQF-IZHYLOQSSA-N n-[2-(dimethylamino)ethyl]-n-[4-[[(z)-(2-oxo-1h-indol-3-ylidene)-phenylmethyl]amino]phenyl]methanesulfonamide Chemical compound C1=CC(N(CCN(C)C)S(C)(=O)=O)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=CC=C2NC\1=O SGVAUCIEUYKEQF-IZHYLOQSSA-N 0.000 claims description 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 125000006603 (C1-C3) alkylaminosulfonyl group Chemical group 0.000 claims description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
• 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 2
• 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
• 230000002159 abnormal effect Effects 0.000 claims description 2
• 150000003855 acyl compounds Chemical class 0.000 claims description 2
• 125000002947 alkylene group Chemical group 0.000 claims description 2
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
• 125000004429 atom Chemical group 0.000 claims description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
• 125000001072 heteroaryl group Chemical group 0.000 claims description 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
• 150000007522 mineralic acids Chemical class 0.000 claims description 2
• 150000007524 organic acids Chemical class 0.000 claims description 2
• 239000001301 oxygen Substances 0.000 claims description 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
• 238000005932 reductive alkylation reaction Methods 0.000 claims description 2
• 230000002829 reductive effect Effects 0.000 claims description 2
• 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 claims description 2
• 125000001589 carboacyl group Chemical group 0.000 claims 3
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
• 125000001721 carboxyacetyl group Chemical group 0.000 claims 1
• 239000003814 drug Substances 0.000 claims 1
• 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims 1
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
• 230000000144 pharmacologic effect Effects 0.000 abstract description 6
• 102000001253 Protein Kinase Human genes 0.000 abstract description 3
• 108060006633 protein kinase Proteins 0.000 abstract description 3
• 102000027426 receptor tyrosine kinases Human genes 0.000 abstract description 3
• 108091008598 receptor tyrosine kinases Proteins 0.000 abstract description 3
• 230000003612 virological effect Effects 0.000 abstract description 3
• 239000013067 intermediate product Substances 0.000 abstract 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 681
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 378
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 319
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 318
• 238000001819 mass spectrum Methods 0.000 description 293
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 171
• 229910052799 carbon Inorganic materials 0.000 description 161
• 239000000047 product Substances 0.000 description 153
• 238000002844 melting Methods 0.000 description 139
• 230000008018 melting Effects 0.000 description 139
• 239000000243 solution Substances 0.000 description 126
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 108
• 239000000741 silica gel Substances 0.000 description 107
• 229910002027 silica gel Inorganic materials 0.000 description 107
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 93
• 238000011282 treatment Methods 0.000 description 90
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 86
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 71
• 238000004458 analytical method Methods 0.000 description 66
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 57
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 47
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
• 239000002904 solvent Substances 0.000 description 45
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 42
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
• 239000011541 reaction mixture Substances 0.000 description 40
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 38
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 38
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 38
• RQFHATRKMMVQPC-UHFFFAOYSA-N 1-acetyl-3-[ethoxy(phenyl)methylidene]-5-nitroindol-2-one Chemical compound O=C1N(C(C)=O)C2=CC=C([N+]([O-])=O)C=C2C1=C(OCC)C1=CC=CC=C1 RQFHATRKMMVQPC-UHFFFAOYSA-N 0.000 description 33
• 235000011114 ammonium hydroxide Nutrition 0.000 description 33
• 239000000203 mixture Substances 0.000 description 33
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 30
• QNWGMJXVSLRFMR-UHFFFAOYSA-N 1-acetyl-3-[ethoxy(phenyl)methylidene]indol-2-one Chemical compound O=C1N(C(C)=O)C2=CC=CC=C2C1=C(OCC)C1=CC=CC=C1 QNWGMJXVSLRFMR-UHFFFAOYSA-N 0.000 description 27
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
• CQMHZLKNXHIIOT-UHFFFAOYSA-N 3-[ethoxy(phenyl)methylidene]-5-nitro-1h-indol-2-one Chemical compound O=C1NC2=CC=C([N+]([O-])=O)C=C2C1=C(OCC)C1=CC=CC=C1 CQMHZLKNXHIIOT-UHFFFAOYSA-N 0.000 description 25
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 25
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 22
• 229960000583 acetic acid Drugs 0.000 description 21
• 238000000354 decomposition reaction Methods 0.000 description 20
• 238000000967 suction filtration Methods 0.000 description 20
• 239000012317 TBTU Substances 0.000 description 19
• CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 19
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 18
• 239000012362 glacial acetic acid Substances 0.000 description 16
• NNCCQALFJIMRKB-UHFFFAOYSA-N 4-[(dimethylamino)methyl]aniline Chemical compound CN(C)CC1=CC=C(N)C=C1 NNCCQALFJIMRKB-UHFFFAOYSA-N 0.000 description 14
• 239000003054 catalyst Substances 0.000 description 14
• 238000001816 cooling Methods 0.000 description 14
• 239000002244 precipitate Substances 0.000 description 14
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 12
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
• 239000002253 acid Substances 0.000 description 12
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 12
• 239000002585 base Substances 0.000 description 12
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
• 210000004027 cell Anatomy 0.000 description 11
• OANCBHUMQGJXQG-UHFFFAOYSA-N 1-acetyl-3-[methoxy(phenyl)methylidene]-5-nitroindol-2-one Chemical compound O=C1N(C(C)=O)C2=CC=C([N+]([O-])=O)C=C2C1=C(OC)C1=CC=CC=C1 OANCBHUMQGJXQG-UHFFFAOYSA-N 0.000 description 10
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Substances CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 10
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 9
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
• 238000003776 cleavage reaction Methods 0.000 description 9
• 239000012074 organic phase Substances 0.000 description 9
• 239000003208 petroleum Substances 0.000 description 9
• 230000007017 scission Effects 0.000 description 9
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
• 125000002252 acyl group Chemical group 0.000 description 8
• CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 8
• WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 238000010992 reflux Methods 0.000 description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
• JWNSTRPJMURHFG-VXPUYCOJSA-N (3z)-3-[(4-aminoanilino)-phenylmethylidene]-1h-indol-2-one Chemical compound C1=CC(N)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=CC=C2NC\1=O JWNSTRPJMURHFG-VXPUYCOJSA-N 0.000 description 7
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