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【结 构 式】 
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【药物名称】 【化学名称】3-[2-Bromo-4-(isopropyl)phenyl]-7-(diethylamino)-5-methylthiazolo[4,5-d]pyrimidine-2(3H)-thione 【CA登记号】 【 分 子 式 】C19H23BrN4S2 【 分 子 量 】451.45396 |
【开发单位】Bristol-Myers Squibb (Originator) 【药理作用】Antidepressants, Anxiolytics, Mood Disorders, Treatment of, PSYCHOPHARMACOLOGIC DRUGS, CRF1 Antagonists |
合成路线1
Aniline (I) was converted to the isothiocyanate (II) using thiophosgene in DMF, and then treated with cyanoacetamide and sulfur to afford thiazolothione (III). Subsequent reaction of (III) with acetic anhydride generated the pyrimidine (IV), which was chlorinated with refluxing POCl3 to give (V). Finally, condensation of (V) with diethylamine in boiling acetone furnished the target compound.
| 【1】 Beck, J.P.; et al.; Thiazolo[4,5-d]pyrimidine thiones and -ones as corticotropin-releasing hormone (CRH-R1) receptor antagonists. Bioorg Med Chem Lett 1999, 9, 8, 1185. |
| 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) | 23782 | 2-bromo-4-isopropylaniline; 2-bromo-4-isopropylphenylamine | 51605-97-1 | C9H12BrN | 详情 | 详情 |
| (II) | 27728 | 2-bromo-4-isopropyl-1-isothiocyanatobenzene | C10H10BrNS | 详情 | 详情 | |
| (III) | 27729 | 4-amino-3-(2-bromo-4-isopropylphenyl)-2-thioxo-2,3-dihydro-1,3-thiazole-5-carboxamide | C13H14BrN3OS2 | 详情 | 详情 | |
| (IV) | 27730 | 3-(2-bromo-4-isopropylphenyl)-5-methyl-2-thioxo-2,3-dihydro[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one | C15H14BrN3OS2 | 详情 | 详情 | |
| (V) | 27731 | 3-(2-bromo-4-isopropylphenyl)-7-chloro-5-methyl[1,3]thiazolo[4,5-d]pyrimidine-2(3H)-thione | C15H13BrClN3S2 | 详情 | 详情 |
Extended Information