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【结 构 式】 
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【分子编号】35578 【品名】tert-butyl 2-[[(3S)-3-amino-2-oxopyrrolidinyl]methyl]-1H-pyrrolo[2,3-c]pyridine-1-carboxylate 【CA登记号】 |
【 分 子 式 】C17H22N4O3 【 分 子 量 】330.38684 【元素组成】C 61.8% H 6.71% N 16.96% O 14.53% |
合成路线1
该中间体在本合成路线中的序号：(XVII)N-alkylation of (S)-3-(benzyloxycarbonylamino)-2-pyrrolidinone (XIII) with propargyl bromide produced (XIV). Palladium-mediated coupling (XIV) with iodopyridine (X) gave adduct (XV), which was cyclized to the pyrrolopyridine (XVI) by means of DBU. The benzyloxycarbonyl protecting group of (XVI) was removed by transfer catalytic hydrogenolysis with formic acid, and the deprotected amine (XVII) was then condensed with sulfonyl chloride (VII) to furnish sulfonamide (XII). Deprotection of the Boc group of (XII) as above gave rise to the title compound.
| 【1】 Choi-Sledeski, Y.M.; Becker, M.R.; Pauls, H.W.; et al.; Azaindole pyrrolidinone inhibitors of factor Xa: SAR, synthesis, and X-ray crystal structure of a novel surrogate for basic P1 moieties. 218th ACS Natl Meet (Aug 22 1999, New Orleans) 1999, Abst MEDI 33. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 11176 | 3-Bromopropyne; 3-Bromo-1-propyne | 106-96-7 | C3H3Br | 详情 | 详情 | |
| (VII) | 29496 | thieno[3,2-b]pyridine-2-sulfonyl chloride | C7H4ClNO2S2 | 详情 | 详情 | |
| (X) | 35571 | tert-butyl 4-iodo-3-pyridinylcarbamate | C10H13IN2O2 | 详情 | 详情 | |
| (XII) | 35573 | tert-butyl 2-([(3S)-2-oxo-3-[(thieno[3,2-b]pyridin-2-ylsulfonyl)amino]pyrrolidinyl]methyl)-1H-pyrrolo[2,3-c]pyridine-1-carboxylate | C24H25N5O5S2 | 详情 | 详情 | |
| (XIII) | 35574 | benzyl (3S)-2-oxopyrrolidinylcarbamate | C12H14N2O3 | 详情 | 详情 | |
| (XIV) | 35575 | benzyl (3S)-2-oxo-1-(2-propynyl)pyrrolidinylcarbamate | C15H16N2O3 | 详情 | 详情 | |
| (XV) | 35576 | benzyl (3S)-1-(3-[3-[(tert-butoxycarbonyl)amino]-4-pyridinyl]-2-propynyl)-2-oxopyrrolidinylcarbamate | C25H28N4O5 | 详情 | 详情 | |
| (XVI) | 35577 | tert-butyl 2-[((3S)-3-[[(benzyloxy)carbonyl]amino]-2-oxopyrrolidinyl)methyl]-1H-pyrrolo[2,3-c]pyridine-1-carboxylate | C25H28N4O5 | 详情 | 详情 | |
| (XVII) | 35578 | tert-butyl 2-[[(3S)-3-amino-2-oxopyrrolidinyl]methyl]-1H-pyrrolo[2,3-c]pyridine-1-carboxylate | C17H22N4O3 | 详情 | 详情 |