|
【结 构 式】 
|
【分子编号】27824 【品名】4-[[(2,2,2-trifluoroacetyl)amino]methyl]benzoic acid 【CA登记号】 |
【 分 子 式 】C10H8F3NO3 【 分 子 量 】247.1736696 【元素组成】C 48.59% H 3.26% F 23.06% N 5.67% O 19.42% |
合成路线1
该中间体在本合成路线中的序号：(II)The acylation of 4-(aminomethyl)benzoic acid (I) with trifluoroacetic anhydride gives the corresponding trifluoroacetamide (II), which is condensed with the monoprotected ortho-phenylenediamine (III) by means of oxalyl chloride in dichloromethane/DMF yielding the benzamide (IV). Elimination of the trifluoacetyl group of (V) by means of K2CO3 in methanol/water affords the 4-(aminomethyl)-derivative (V), which is condensed with 3-(hydroxymethyl)pyridine (VI) and carbonyldiimidazole (CDI) in THF providing the Boc-protected intermediate (VII). Finally, this compound is deprotected by a treatment with 4N HCl in dioxane/water.
| 【1】 Suzuki, T.; Ando, T.; Tsuchiya, K.; Nakanishi, O.; Saito, A.; Yamashita, T.; Shiraishi, Y.; Tanaka, E. (Mitsui Chemicals, Inc.); Benzamide derivs., useful as cell differentiation inducers. EP 0847992 . |
| 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) | 27823 | 4-(aminomethyl)benzoic acid | 56-91-7 | C8H9NO2 | 详情 | 详情 |
| (II) | 27824 | 4-[[(2,2,2-trifluoroacetyl)amino]methyl]benzoic acid | C10H8F3NO3 | 详情 | 详情 | |
| (III) | 27825 | tert-butyl 2-aminophenylcarbamate | C11H16N2O2 | 详情 | 详情 | |
| (IV) | 27826 | tert-butyl 2-[(4-[[(2,2,2-trifluoroacetyl)amino]methyl]benzoyl)amino]phenylcarbamate | C21H22F3N3O4 | 详情 | 详情 | |
| (V) | 27827 | tert-butyl 2-[[4-(aminomethyl)benzoyl]amino]phenylcarbamate | C19H23N3O3 | 详情 | 详情 | |
| (VI) | 15798 | 3-Pyridinemethanol; 3-pyridinylmethanol | 100-55-0 | C6H7NO | 详情 | 详情 |
| (VII) | 27828 | 3-pyridinylmethyl 4-([2-[(tert-butoxycarbonyl)amino]anilino]carbonyl)benzylcarbamate | C26H28N4O5 | 详情 | 详情 |