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【结 构 式】 
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【分子编号】33252 【品名】5-(2-bromoacetyl)-2-thiophenecarboxamide 【CA登记号】 |
【 分 子 式 】C7H6BrNO2S 【 分 子 量 】248.10018 【元素组成】C 33.89% H 2.44% Br 32.21% N 5.65% O 12.9% S 12.92% |
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：(III)The reaction of 5-carboxy-2-acetylthiophene (I) first with SOCl2 in refluxing toluene, and then with aqueous ammonia gives 5-carbamoyl-2-acetylthiophene (II), which is brominated with Br2 in hot acetic acid yielding 5-carbamoyl-2-bromoacetylthiophene (III). The cyclization of (III) with ammonium dithiocarbamate (A) in refluxing methanol-DMF affords 2-mercapto-4-(5'-carbamoyl-2'-thienyl)thiazole (IV), which is finally condensed with 1-chloro-3-tert-butylaminoisopropanol (V) by means of NaOH in water methanol.
| 【1】 Hara, Y.; et al.; Synthesis and beta-adrenergic blocking action of a new thiazolylthiopropanolamine derivative. J Pharm Sci 1978, 67, 1334-35. |
| 【2】 Hibino, T.; et al.; JP 7525562 . |
| 【3】 Hibino, T.; et al.; JP 7576069 . |
| 【4】 Hibino, T.; et al. (Sumitomo Chemical Co., Ltd.); Thiazole derivatives. DE 2341753; FR 2196162; GB 1435139; NL 7311248; US 3932400 . |
| 【5】 Reiner, A. (SkyePharma AG); Process for preparing ursodeoxycholic acid derivates and their inorganic and organic salts having therapeutic activity. EP 0272462 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 33253 | ammonium carbamodithioate | CH6N2S2 | 详情 | 详情 | |
| (I) | 33250 | 5-acetyl-2-thiophenecarboxylic acid | 4066-41-5 | C7H6O3S | 详情 | 详情 |
| (II) | 33251 | 5-acetyl-2-thiophenecarboxamide | C7H7NO2S | 详情 | 详情 | |
| (III) | 33252 | 5-(2-bromoacetyl)-2-thiophenecarboxamide | C7H6BrNO2S | 详情 | 详情 | |
| (IV) | 33254 | 5-(2-sulfanyl-1,3-thiazol-4-yl)-2-thiophenecarboxamide | C8H6N2OS3 | 详情 | 详情 | |
| (V) | 31720 | 1-(tert-butylamino)-3-chloro-2-propanol | C7H16ClNO | 详情 | 详情 |
Extended Information