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【结 构 式】 
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【分子编号】62969 【品名】3-[acetyl(methyl)amino]phenylboronic acid 【CA登记号】 |
【 分 子 式 】C9H12BNO3 【 分 子 量 】193.01022 【元素组成】C 56.01% H 6.27% B 5.6% N 7.26% O 24.87% |
合成路线1
该中间体在本合成路线中的序号：(XXVI)Cyclization of 5-aminopyrazole-4-carboxylic acid ethyl ester (XXI) with either, 3,3-diethoxypropionic acid ethyl ester (XXII) or 3-oxopropionic acid ethyl ester (XXIII) in refluxing AcOH gives 7-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester (XXIV), which is treated with POCl3 to yield the corresponding chloro derivative (XXV). Condensation of compound (XXV) with 3-(N-methylacetamido)phenylboronic acid (XXVI) by means of Pd(PPh3)4 and Na2CO3 in ethanol affords the pyrazolo-[1,5-a]pyrimidine-carboxylic acid ethyl ester (XXVII), which is finally condensed with 2-bromothiophene (XX) and Mg.
| 【1】 Sorbera, L.A.; Castaner, J.; Martin, L.; Indiplon. Drugs Fut 2003, 28, 8, 739. |
| 【2】 Wilcoxen, K.M.; Gross, R.S. (Neurocrine Biosciences Inc.); Synthesis of substd. pyrazolopyrimidines. WO 0110868 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XX) | 13681 | 2-Bromothiophene | 1003-09-4 | C4H3BrS | 详情 | 详情 |
| (XXI) | 51140 | 3-Amino-4-pyrazolecarboxylic acid ethyl ester; Ethyl 3-aminopyrazole-4-carboxylate; 3-Amino-4-carbethoxypyrazole | 6994-25-8 | C6H9N3O2 | 详情 | 详情 |
| (XXII) | 17901 | Ethyl 3,3-diethoxypropanoate | 10601-80-6 | C9H18O4 | 详情 | 详情 |
| (XXIII) | 62966 | ethyl 3-oxopropanoate | C5H8O3 | 详情 | 详情 | |
| (XXIV) | 62967 | ethyl 7-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxylate | C9H9N3O3 | 详情 | 详情 | |
| (XXV) | 62968 | ethyl 7-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate | C9H8ClN3O2 | 详情 | 详情 | |
| (XXVI) | 62969 | 3-[acetyl(methyl)amino]phenylboronic acid | C9H12BNO3 | 详情 | 详情 | |
| (XXVII) | 62970 | ethyl 7-{3-[acetyl(methyl)amino]phenyl}pyrazolo[1,5-a]pyrimidine-3-carboxylate | C18H18N4O3 | 详情 | 详情 |