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【结 构 式】 
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【分子编号】42916 【品名】3-isopropoxy-5-methoxy-1-phenyl-N-(1H-1,2,3,4-tetraazol-5-yl)-1H-indole-2-carboxamide 【CA登记号】 |
【 分 子 式 】C20H20N6O3 【 分 子 量 】392.41744 【元素组成】C 61.22% H 5.14% N 21.42% O 12.23% |
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：(VI)The alkylation of 3-hydroxy-5-methoxy-1-phenylindole-2-carboxylic acid methyl ester (I) with isopropyl bromide (II) and KOH gives the corresponding 2-isopropoxy compound (III), which is hydrolyzed with KOH and HOAc, yielding the carboxylic acid (IV). The condensation of (IV) with 1H-tetrazol-5-amine (V) by means of CDI affords the expected amide (VI), which is finally treated with L-arginine to furnish the target arginine salt.
| 【1】 Unangst, P.C.; Carethers, M.E.; Indole esters as heterocyclic synthons. III. Preparation and reactions of furo[3,2-b]indoles. J Heterocycl Chem 1984, 21, 709-714. |
| 【2】 Kunz, K.; Friendlander, P.; Concerning N,N'-diphenyl-indigo. Chem Ber 1922, 55, 1597-1607. |
| 【3】 Unangst, P.C.; Conroy, M.C.; CI-949 AND RELATED INDOLECARBOXAMIDOTETRAZOLES: A NEW CLASS OF POTENTIAL ANTIALLERGY AGENTS. Drugs Fut 1990, 15, 10, 1005. |
| 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) | 42913 | methyl 3-hydroxy-5-methoxy-1-phenyl-1H-indole-2-carboxylate | C17H15NO4 | 详情 | 详情 | |
| (II) | 32658 | 2-bromopropane | 75-26-3 | C3H7Br | 详情 | 详情 |
| (III) | 42914 | methyl 3-isopropoxy-5-methoxy-1-phenyl-1H-indole-2-carboxylate | C20H21NO4 | 详情 | 详情 | |
| (IV) | 42915 | 3-isopropoxy-5-methoxy-1-phenyl-1H-indole-2-carboxylic acid | C19H19NO4 | 详情 | 详情 | |
| (V) | 14092 | 1H-1,2,3,4-Tetraazol-5-ylamine; 1H-Tetrazol-5-amine; 1H-1,2,3,4-Tetraazol-5-amine; 5-Amino-1H-1,2,3,4-tetrazole | 4418-61-5 | CH3N5 | 详情 | 详情 |
| (VI) | 42916 | 3-isopropoxy-5-methoxy-1-phenyl-N-(1H-1,2,3,4-tetraazol-5-yl)-1H-indole-2-carboxamide | C20H20N6O3 | 详情 | 详情 | |
| (VII) | 42917 | L-2-Amino-5-guanidinopentanoic acid; (S)-(+)-Arginine; L-Arginine | 74-79-3 | C6H14N4O2 | 详情 | 详情 |
Extended Information