methyl 6-[[(Z)-1-methoxyethylidene]amino]-5-([[(3R)-9-nitro-4-oxo-1-phenyl-3,4,6,7-tetrahydro[1,4]diazepino[6,7,1-hi]indol-3-yl]amino]carbonyl)-2-pyridinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】48354

【品名】methyl 6-[[(Z)-1-methoxyethylidene]amino]-5-([[(3R)-9-nitro-4-oxo-1-phenyl-3,4,6,7-tetrahydro[1,4]diazepino[6,7,1-hi]indol-3-yl]amino]carbonyl)-2-pyridinecarboxylate

【CA登记号】

【分子式】C₂₈H₂₄N₆O₇

【分子量】556.5348

【元素组成】C 60.43% H 4.35% N 15.1% O 20.12%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(V)

3(R)-Amino-1-phenyl-6,7-dihydro-3H-[1,4]diazepin[6,7,1-hi]indol-4-one (I) was nitrated using KNO3 in concentrated H2SO4 to furnish the 9-nitro derivative (II). Coupling of (II) with 2-amino-6-(methoxycarbonyl)pyridine-3-carboxylic acid (III) in the presence of DCC and HOBt gave amide (IV). Imidate (V) was prepared by heating (IV) with trimethyl orthoacetate under vacuum distillation of the generated MeOH. Cyclization of (V) to produce the target pyridopyrimidine system (VI) was achieved using scandium triflate as the catalyst. The nitro group was finally hydrogenated over Ru/C to yield the title amino derivative.

参考文献中间体

合成目标

【1】 Bernardelli, P. (Pfizer Inc.); Method for preparing substd. [1,4]diazepino[6,7,1-hi]indol-4-ones. FR 2795731; WO 0102403 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	47459	(3R)-3-amino-1-phenyl-6,7-dihydro[1,4]diazepino[6,7,1-hi]indol-4(3H)-one	C₁₇H₁₅N₃O	详情	详情
(II)	47460	(3R)-3-amino-9-nitro-1-phenyl-6,7-dihydro[1,4]diazepino[6,7,1-hi]indol-4(3H)-one	C₁₇H₁₄N₄O₃	详情	详情
(III)	48352	2-amino-6-(methoxycarbonyl)nicotinic acid	C₈H₈N₂O₄	详情	详情
(IV)	48353	methyl 6-amino-5-([[(3R)-9-nitro-4-oxo-1-phenyl-3,4,6,7-tetrahydro[1,4]diazepino[6,7,1-hi]indol-3-yl]amino]carbonyl)-2-pyridinecarboxylate	C₂₅H₂₀N₆O₆	详情	详情
(V)	48354	methyl 6-[[(Z)-1-methoxyethylidene]amino]-5-([[(3R)-9-nitro-4-oxo-1-phenyl-3,4,6,7-tetrahydro[1,4]diazepino[6,7,1-hi]indol-3-yl]amino]carbonyl)-2-pyridinecarboxylate	C₂₈H₂₄N₆O₇	详情	详情
(VI)	48355	methyl 2-methyl-3-[(3S)-9-nitro-4-oxo-1-phenyl-3,4,6,7-tetrahydro[1,4]diazepino[6,7,1-hi]indol-3-yl]-4-oxo-3,4-dihydropyrido[2,3-d]pyrimidine-7-carboxylate	C₂₇H₂₀N₆O₆	详情	详情

Extended Information