NO323766B1 - Azaindoler, farmasoytiske sammensetninger innbefattende og deres anvendelse for fremstilling av medikament - Google Patents

Info

Publication number

NO323766B1

NO323766B1 NO20023032A NO20023032A NO323766B1 NO 323766 B1 NO323766 B1 NO 323766B1 NO 20023032 A NO20023032 A NO 20023032A NO 20023032 A NO20023032 A NO 20023032A NO 323766 B1 NO323766 B1 NO 323766B1

Authority

NO

Norway

Prior art keywords

pyrrolo

methyl

compound according

alkyl

optionally substituted

Prior art date

1999-12-24

Links

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• 239000003814 drug Substances 0.000 title claims description 23
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
• 238000004519 manufacturing process Methods 0.000 title claims description 4
• 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims description 453
• 239000000203 mixture Substances 0.000 claims description 158
• 125000000217 alkyl group Chemical group 0.000 claims description 125
• 229910052739 hydrogen Inorganic materials 0.000 claims description 92
• 239000001257 hydrogen Substances 0.000 claims description 91
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 86
• 150000003839 salts Chemical class 0.000 claims description 70
• -1 cyclic acetal Chemical class 0.000 claims description 67
• 125000001072 heteroaryl group Chemical group 0.000 claims description 63
• 229940002612 prodrug Drugs 0.000 claims description 62
• 239000000651 prodrug Substances 0.000 claims description 62
• 125000003118 aryl group Chemical group 0.000 claims description 56
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 52
• 239000002253 acid Substances 0.000 claims description 50
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 46
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 42
• 150000002148 esters Chemical class 0.000 claims description 41
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
• 150000002431 hydrogen Chemical class 0.000 claims description 36
• 238000011282 treatment Methods 0.000 claims description 35
• 239000012453 solvate Substances 0.000 claims description 33
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
• 125000005843 halogen group Chemical group 0.000 claims description 28
• 150000001204 N-oxides Chemical class 0.000 claims description 27
• 150000004677 hydrates 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 23
• 108091000080 Phosphotransferase Proteins 0.000 claims description 22
• 102000020233 phosphotransferase Human genes 0.000 claims description 22
• 125000003342 alkenyl group Chemical group 0.000 claims description 21
• 238000002360 preparation method Methods 0.000 claims description 20
• 229940079593 drug Drugs 0.000 claims description 19
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 19
• 125000003107 substituted aryl group Chemical group 0.000 claims description 18
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• 206010028980 Neoplasm Diseases 0.000 claims description 14
• 125000001475 halogen functional group Chemical group 0.000 claims description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 11
• 125000001041 indolyl group Chemical group 0.000 claims description 11
• 229920006395 saturated elastomer Polymers 0.000 claims description 11
• 230000002401 inhibitory effect Effects 0.000 claims description 10
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 10
• 125000001424 substituent group Chemical group 0.000 claims description 9
• 125000002252 acyl group Chemical group 0.000 claims description 8
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 8
• 230000003197 catalytic effect Effects 0.000 claims description 8
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
• 201000011510 cancer Diseases 0.000 claims description 7
• 125000004122 cyclic group Chemical group 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
• 125000001931 aliphatic group Chemical group 0.000 claims description 6
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
• 206010003246 arthritis Diseases 0.000 claims description 6
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 6
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 125000005842 heteroatom Chemical group 0.000 claims description 5
• 125000002950 monocyclic group Chemical group 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 201000004681 Psoriasis Diseases 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 208000006673 asthma Diseases 0.000 claims description 4
• 229910052799 carbon Inorganic materials 0.000 claims description 4
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
• 239000003112 inhibitor Substances 0.000 claims description 4
• 208000018937 joint inflammation Diseases 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• FTJGHPGHUSLQAK-UHFFFAOYSA-N 2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridine-4-carbonitrile Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC)=CC2=C1C#N FTJGHPGHUSLQAK-UHFFFAOYSA-N 0.000 claims description 3
• CNJGCQXKBAUFNA-UHFFFAOYSA-N 4-(3-methyl-1h-pyrrolo[2,3-b]pyridin-2-yl)benzoic acid Chemical compound N1C2=NC=CC=C2C(C)=C1C1=CC=C(C(O)=O)C=C1 CNJGCQXKBAUFNA-UHFFFAOYSA-N 0.000 claims description 3
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 3
• 150000002894 organic compounds Chemical class 0.000 claims description 3
• QBUASRVBPRBVRJ-UHFFFAOYSA-N 1-[1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-5-yl]oxycyclobutane-1-carboxamide Chemical compound C=1C=C2N(C)C=C(C=3NC4=NC=CC=C4C=3)C2=CC=1OC1(C(N)=O)CCC1 QBUASRVBPRBVRJ-UHFFFAOYSA-N 0.000 claims description 2
• QOWCSDWRCIPYJJ-UHFFFAOYSA-N 2-(4-bromophenyl)-3-methyl-1h-pyrrolo[2,3-b]pyridine Chemical compound N1C2=NC=CC=C2C(C)=C1C1=CC=C(Br)C=C1 QOWCSDWRCIPYJJ-UHFFFAOYSA-N 0.000 claims description 2
• PAUWEYGKUDICMQ-UHFFFAOYSA-N 2-(4-chlorophenyl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CC(Cl)=CC=C1C1=CC2=CC=CN=C2N1 PAUWEYGKUDICMQ-UHFFFAOYSA-N 0.000 claims description 2
• SHISXEDJQZVJAL-UHFFFAOYSA-N 2-(4-methoxyphenyl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CC(OC)=CC=C1C1=CC2=CC=CN=C2N1 SHISXEDJQZVJAL-UHFFFAOYSA-N 0.000 claims description 2
• UNQRREMUTOUZSE-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-methyl-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CC(OC)=CC=C1C1=C(C)C2=CC=CN=C2N1 UNQRREMUTOUZSE-UHFFFAOYSA-N 0.000 claims description 2
• PPWLAQVKIFDULF-UHFFFAOYSA-N 2-phenyl-1h-pyrrolo[2,3-b]pyridine Chemical compound N1C2=NC=CC=C2C=C1C1=CC=CC=C1 PPWLAQVKIFDULF-UHFFFAOYSA-N 0.000 claims description 2
• ALSYTSCUTDAYIU-UHFFFAOYSA-N 2-pyridin-3-yl-1h-pyrrolo[2,3-b]pyridine Chemical compound N1C2=NC=CC=C2C=C1C1=CC=CN=C1 ALSYTSCUTDAYIU-UHFFFAOYSA-N 0.000 claims description 2
• UGBJLTPTFVECSC-UHFFFAOYSA-N 3-methyl-2-phenyl-1h-pyrrolo[2,3-b]pyridine Chemical compound N1C2=NC=CC=C2C(C)=C1C1=CC=CC=C1 UGBJLTPTFVECSC-UHFFFAOYSA-N 0.000 claims description 2
• PPRZWBLCPANUPB-UHFFFAOYSA-N 4-methyl-2-phenyl-1h-pyrrolo[2,3-b]pyridine Chemical compound C=1C=2C(C)=CC=NC=2NC=1C1=CC=CC=C1 PPRZWBLCPANUPB-UHFFFAOYSA-N 0.000 claims description 2
• LQAFCJAXORNEHL-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-pyrrolo[2,3-b]pyridine Chemical compound C=1C2=CC(C)=CN=C2NC=1C1=CC=CC=C1 LQAFCJAXORNEHL-UHFFFAOYSA-N 0.000 claims description 2
• 229910014033 C-OH Inorganic materials 0.000 claims description 2
• 229910014570 C—OH Inorganic materials 0.000 claims description 2
• UVPSSGJTBLNVRE-UHFFFAOYSA-N Moniliformin Natural products O=C1C(OC)=CC(=O)C=2C1=C1C(=O)C(OC)=CC(=O)C1=CC=2 UVPSSGJTBLNVRE-UHFFFAOYSA-N 0.000 claims description 2
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
• 125000004442 acylamino group Chemical group 0.000 claims description 2
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
• 125000004414 alkyl thio group Chemical group 0.000 claims description 2
• 125000003435 aroyl group Chemical group 0.000 claims description 2
• 125000005239 aroylamino group Chemical group 0.000 claims description 2
• 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 2
• 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 2
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
• 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 2
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
• 125000005110 aryl thio group Chemical group 0.000 claims description 2
• 125000004104 aryloxy group Chemical group 0.000 claims description 2
• 125000002541 furyl group Chemical group 0.000 claims description 2
• 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 2
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 2
• 125000002883 imidazolyl group Chemical group 0.000 claims description 2
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
• 208000027866 inflammatory disease Diseases 0.000 claims description 2
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
• KGPQKNJSZNXOPV-UHFFFAOYSA-N moniliformin Chemical compound OC1=CC(=O)C1=O KGPQKNJSZNXOPV-UHFFFAOYSA-N 0.000 claims description 2
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
• 101100256910 Drosophila melanogaster sick gene Proteins 0.000 claims 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
• UPAYIGZHWMYXCV-UHFFFAOYSA-N 3-methyl-2-(4-methylphenyl)-1h-pyrrolo[2,3-b]pyridine Chemical compound N1C2=NC=CC=C2C(C)=C1C1=CC=C(C)C=C1 UPAYIGZHWMYXCV-UHFFFAOYSA-N 0.000 claims 1
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
• QCMDUUAPARGBIF-UHFFFAOYSA-N methyl 4-(3-methyl-1h-pyrrolo[2,3-b]pyridin-2-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=C(C)C2=CC=CN=C2N1 QCMDUUAPARGBIF-UHFFFAOYSA-N 0.000 claims 1
• ITJRVXVDBRQCJG-UHFFFAOYSA-N propan-2-yl 4-(3-methyl-1h-pyrrolo[2,3-b]pyridin-2-yl)benzoate Chemical compound C1=CC(C(=O)OC(C)C)=CC=C1C1=C(C)C2=CC=CN=C2N1 ITJRVXVDBRQCJG-UHFFFAOYSA-N 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 406
• 239000007787 solid Substances 0.000 description 319
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 198
• 239000000243 solution Substances 0.000 description 195
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 155
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 146
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 124
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 123
• 238000002844 melting Methods 0.000 description 105
• 230000008018 melting Effects 0.000 description 105
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 95
• 238000000034 method Methods 0.000 description 92
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 73
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 72
• 239000011541 reaction mixture Substances 0.000 description 72
• 238000006243 chemical reaction Methods 0.000 description 64
• 238000005481 NMR spectroscopy Methods 0.000 description 63
• 238000004128 high performance liquid chromatography Methods 0.000 description 62
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 54
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 53
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 52
• IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 47
• 210000004027 cell Anatomy 0.000 description 46
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
• 238000003756 stirring Methods 0.000 description 45
• 239000000377 silicon dioxide Substances 0.000 description 43
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 41
• 238000004809 thin layer chromatography Methods 0.000 description 40
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 37
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 36
• 235000019341 magnesium sulphate Nutrition 0.000 description 36
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 33
• 210000004072 lung Anatomy 0.000 description 33
• 229910052757 nitrogen Inorganic materials 0.000 description 32
• 238000010992 reflux Methods 0.000 description 32
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• 230000000875 corresponding effect Effects 0.000 description 31
• 230000000694 effects Effects 0.000 description 31
• 239000012267 brine Substances 0.000 description 29
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 29
• 239000012442 inert solvent Substances 0.000 description 28
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
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• 239000000284 extract Substances 0.000 description 24
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• 230000005764 inhibitory process Effects 0.000 description 23
• 229910052938 sodium sulfate Inorganic materials 0.000 description 23
• 235000011152 sodium sulphate Nutrition 0.000 description 23
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 22
• 239000002585 base Substances 0.000 description 22
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
• 239000010410 layer Substances 0.000 description 20
• 239000000725 suspension Substances 0.000 description 20
• YTWCODZNNZBQFV-KBXCAEBGSA-N (1R,2R)-2-[[4-(2-fluoro-5-propan-2-yloxyphenyl)phenoxy]methyl]cyclopropane-1-carboxylic acid Chemical compound FC1=C(C=C(C=C1)OC(C)C)C1=CC=C(C=C1)OC[C@H]1[C@@H](C1)C(=O)O YTWCODZNNZBQFV-KBXCAEBGSA-N 0.000 description 19
• 239000002904 solvent Substances 0.000 description 19
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 18
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 18
• 230000008569 process Effects 0.000 description 18
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• 102000016621 Focal Adhesion Protein-Tyrosine Kinases Human genes 0.000 description 16
• 108010067715 Focal Adhesion Protein-Tyrosine Kinases Proteins 0.000 description 16
• 241001465754 Metazoa Species 0.000 description 15
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
• 241000700159 Rattus Species 0.000 description 15
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• 102100032311 Aurora kinase A Human genes 0.000 description 14
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 14
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 14
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 14
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
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• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
• 238000000746 purification Methods 0.000 description 14
• 230000004044 response Effects 0.000 description 14
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• 238000012360 testing method Methods 0.000 description 14
• CVDGAVDNVQNYQT-UHFFFAOYSA-N 1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indole-5-carboxylic acid Chemical compound C12=CC(C(O)=O)=CC=C2N(C)C=C1C1=CC2=CC=CN=C2N1 CVDGAVDNVQNYQT-UHFFFAOYSA-N 0.000 description 13
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• 238000000354 decomposition reaction Methods 0.000 description 13
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• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 12
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• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
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• 239000000706 filtrate Substances 0.000 description 11
• 238000003818 flash chromatography Methods 0.000 description 11
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• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 10
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• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
• 229910052794 bromium Inorganic materials 0.000 description 9
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 9
• 229940035423 ethyl ether Drugs 0.000 description 9
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