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【结 构 式】 
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【分子编号】48355 【品名】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 【CA登记号】 |
【 分 子 式 】C27H20N6O6 【 分 子 量 】524.49264 【元素组成】C 61.83% H 3.84% N 16.02% O 18.3% |
合成路线1
该中间体在本合成路线中的序号：(VI)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.
| 【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 | CAS号 | 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 |