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【结 构 式】 
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【分子编号】19831 【品名】(6S)-1-(3,5-dibromobenzyl)-5-(2,2-diphenylacetyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid 【CA登记号】 |
【 分 子 式 】C28H23Br2N3O3 【 分 子 量 】609.31704 【元素组成】C 55.19% H 3.8% Br 26.23% N 6.9% O 7.88% |
合成路线1
该中间体在本合成路线中的序号：(VI)The reaction of 3-phenacyl-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6(S)-carboxylic acid methyl ester (I) with 2,2-diphenylacetic acid (II) gives 5-(2,2-diphenylacetyl)-3-phenacyl-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6(S)-carboxylic acid methyl ester (III), which is condensed with 3,5-dibromobenzyl bromide (IV) in acetic acid yielding the corresponding 1-(3,5-dibromobenzyl) derivative (V). The hydrolysis of the ester group of (V) with NaOH affords the expected free acid (VI), which is condensed with L-proline tert-butyl ester (VII) giving the corresponding N-substituted L-proline ester (VIII). Finall this compound is coupled with phenylboronic acid (IX), catalized with palladium tetrakis(triphenylphosphine) complex.
| 【1】 Kim, D.; et al.; Non-peptide ligands of the human C5a receptor: Structure-activity relationship of a series of tetrahydroimidazopyridines. 213th ACS Natl Meet (April 13-17, San Francisco) 1997, Abst MEDI 088. |
| 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) | 19826 | methyl (6S)-3-(2-oxo-2-phenylethyl)-3a,4,5,6,7,7a-hexahydro-3H-imidazo[4,5-c]pyridine-6-carboxylate | C16H19N3O3 | 详情 | 详情 | |
| (II) | 19827 | 2,2-diphenylacetic acid | 117-34-0 | C14H12O2 | 详情 | 详情 |
| (III) | 19828 | methyl (6S)-5-(2,2-diphenylacetyl)-3-(2-oxo-2-phenylethyl)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylate | C30H27N3O4 | 详情 | 详情 | |
| (IV) | 19829 | 1,3-dibromo-5-(bromomethyl)benzene | 56908-88-4 | C7H5Br3 | 详情 | 详情 |
| (V) | 19830 | methyl (6S)-1-(3,5-dibromobenzyl)-5-(2,2-diphenylacetyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylate | C29H25Br2N3O3 | 详情 | 详情 | |
| (VI) | 19831 | (6S)-1-(3,5-dibromobenzyl)-5-(2,2-diphenylacetyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid | C28H23Br2N3O3 | 详情 | 详情 | |
| (VII) | 19832 | tert-butyl (2S)-2-pyrrolidinecarboxylate | C9H17NO2 | 详情 | 详情 | |
| (VIII) | 19833 | tert-butyl (2S)-1-[[(6S)-1-(3,5-dibromobenzyl)-5-(2,2-diphenylacetyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-6-yl]carbonyl]-2-pyrrolidinecarboxylate | C37H38Br2N4O4 | 详情 | 详情 | |
| (IX) | 16593 | Phenylboronic acid；Benzeneboronic acid;Phenylboron dihydroxide | 98-80-6 | C6H7BO2 | 详情 | 详情 |