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【结 构 式】 
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【分子编号】33449 【品名】2-methyl-2-propenyl 4-(4-amino-6,7,8-trimethoxy-2-quinazolinyl)-1-piperazinecarboxylate 【CA登记号】 |
【 分 子 式 】C20H27N5O5 【 分 子 量 】417.46508 【元素组成】C 57.54% H 6.52% N 16.78% O 19.16% |
合成路线1
该中间体在本合成路线中的序号：(VI)The cyclization of 2-amino-3,4,5-trimethoxybenzoic acid (I) with potassium cyanate in water-acetic acid gives 6,7,8-trimethoxy-2,4-(1H,3H)-quinazolinedione (II), which by refluxing with POCl3 is converted into 6,7,8-trimethoxy-2,4-dichloroquinazoline (III). The reaction of (III) with anhydrous NH3 in THF yields 2-chloro-4-amino-6,7,8-trimethoxyquinazoline (IV), which is then condensed with 2-methylallyl-1-piperazinecarboxylate (V) in refluxing isoamyl alcohol (A) to afford 2-methylallyl-4-(4-amino-6,7,8-trimethoxyquinazolin-2-yl)piperazine-1-carboxylate (VI). Finally, the allyl group of (VI) is hydrated by treating with aqueous sulfuric acid, and converted into the hydrochloride by treatment with ethanolic HCl.
| 【1】 Hess, H.J.; Trialkyloxy quinazolines. DE 2120495; DE 2167157; FR 2092154; GB 1309835; JP 52068191; US 3669968 . |
| 【2】 Castaner, J.; Weetman, D.F.; Trimazosin hydrochloride. Drugs Fut 1978, 3, 4, 325. |
| 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) | 23032 | 3-methyl-1-butanol | 123-51-3 | C5H12O | 详情 | 详情 |
| (I) | 33444 | 2-amino-3,4,5-trimethoxybenzoic acid | 61948-85-4 | C10H13NO5 | 详情 | 详情 |
| (II) | 33445 | 6,7,8-trimethoxy-2,4(1H,3H)-quinazolinedione | C11H12N2O5 | 详情 | 详情 | |
| (III) | 33446 | 2,4-dichloro-6,7,8-trimethoxyquinazoline; 2,4-dichloro-6,7-dimethoxy-8-quinazolinyl methyl ether | C11H10Cl2N2O3 | 详情 | 详情 | |
| (IV) | 33447 | 2-chloro-6,7,8-trimethoxy-4-quinazolinamine; 2-chloro-6,7,8-trimethoxy-4-quinazolinylamine | C11H12ClN3O3 | 详情 | 详情 | |
| (V) | 33448 | 2-methyl-2-propenyl 1-piperazinecarboxylate | C9H16N2O2 | 详情 | 详情 | |
| (VI) | 33449 | 2-methyl-2-propenyl 4-(4-amino-6,7,8-trimethoxy-2-quinazolinyl)-1-piperazinecarboxylate | C20H27N5O5 | 详情 | 详情 |