【结 构 式】 |
【分子编号】64137 【品名】methyl 3-amino-5-{[(2-amino-1,3-thiazol-5-yl)sulfanyl]methyl}benzoate 【CA登记号】 |
【 分 子 式 】C12H13N3O2S2 【 分 子 量 】295.38624 【元素组成】C 48.79% H 4.44% N 14.23% O 10.83% S 21.71% |
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 reductocondensation of 3-amino-5-(chloromethyl)benzoic acid methyl ester (I) with 2-aminothiazol-5-ylisothiocyanate (II) by means of NaBH4 gives the thioether (III), which is condensed with 4-(dimethylamino)benzoyl chloride (IV) by means of pyridine in dichloromethane to yield the amide (V). The hydrolysis of the ester group of (V) with NaOH in methanol affords the corresponding carboxylic acid (VI), which is finally condensed with 1-acetylpiperazine (VII) by means of WSC, HATU and DIEA in THF to provide the target piperazide.
【1】 Wityak, J.; Das, J.; Liu, C.; Lin, J.; Spergel, S.H.; Moquin, R.V.; Furch, J.A.; Doweiko, A.; Kanner, S.; Lin, T.-A.; Selective Emt inhibitors: Discovery and SAR of 2-amino-[(5-thiomethyl)aryl]thiazoles. 225th ACS Natl Meet (March 23 2003, New Orleans) 2003, Abst MEDI 257. |
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) | 64135 | methyl 3-amino-5-(chloromethyl)benzoate | C9H10ClNO2 | 详情 | 详情 | |
(II) | 64136 | 2-amino-1,3-thiazole-5-sulfenyl cyanide | 23056-10-2 | C4H3N3S2 | 详情 | 详情 |
(III) | 64137 | methyl 3-amino-5-{[(2-amino-1,3-thiazol-5-yl)sulfanyl]methyl}benzoate | C12H13N3O2S2 | 详情 | 详情 | |
(IV) | 39988 | 4-(dimethylamino)benzoyl chloride | 4755-50-4 | C9H10ClNO | 详情 | 详情 |
(V) | 64138 | methyl 3-amino-5-{[(2-{[4-(dimethylamino)benzoyl]amino}-1,3-thiazol-5-yl)sulfanyl]methyl}benzoate | C21H22N4O3S2 | 详情 | 详情 | |
(VI) | 64139 | 3-amino-5-{[(2-{[4-(dimethylamino)benzoyl]amino}-1,3-thiazol-5-yl)sulfanyl]methyl}benzoic acid | C20H20N4O3S2 | 详情 | 详情 | |
(VII) | 20674 | N-Acetyl piperazine; 1-(1-piperazinyl)-1-ethanone | 13889-98-0 | C6H12N2O | 详情 | 详情 |
Extended Information