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【结 构 式】 
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【分子编号】58184 【品名】2-hydroxy-4-{[(4-methylphenyl)sulfonyl]amino}benzoic acid 【CA登记号】 |
【 分 子 式 】C14H13NO5S 【 分 子 量 】307.32696 【元素组成】C 54.72% H 4.26% N 4.56% O 26.03% S 10.43% |
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：(XVI)The methylation of 2-hydroxy-4-(4-methylphenylsulfonamido)benzoic acid (XVI) with dimethyl sulfate and KOH in refluxing acetone gives the N,O-dimethylated benzoic acid (XVII), which is chlorinated by means of NCS in hot DMF to yield the chlorobenzoic acid derivative (XVIII). The hydrolysis of (XVIII) with H2SO4 affords 5-chloro-3-methoxy-4-(methylamino)benzoic acid (XIX), which is finally condensed with the aminodiazepine (XV) by means of EDC in dichloromethane to obtain the target chiral benzamide derivative.
| 【1】 Hirokawa, Y.; et al.; Synthesis and structure-activity relationships of 4-amino-5-chloro-N-(1,4-dialkylhexahydro-1,4-diazepin-6-yl)-2-methoxybenzamide derivatives, novel and potent serotonin 5-HT3 and dopamine D2 receptors dual antagonist. Chem Pharm Bull 2002, 50, 7, 941. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XV) | 17802 | (6S)-1-ethyl-4-methyl-1,4-diazepan-6-ylamine; (6S)-1-ethyl-4-methyl-1,4-diazepan-6-amine | C8H19N3 | 详情 | 详情 | |
| (XVI) | 58184 | 2-hydroxy-4-{[(4-methylphenyl)sulfonyl]amino}benzoic acid | C14H13NO5S | 详情 | 详情 | |
| (XVII) | 58185 | 2-methoxy-4-{methyl[(4-methylphenyl)sulfonyl]amino}benzoic acid | C16H17NO5S | 详情 | 详情 | |
| (XVIII) | 58186 | 5-chloro-2-methoxy-4-{methyl[(4-methylphenyl)sulfonyl]amino}benzoic acid | C16H16ClNO5S | 详情 | 详情 | |
| (XIX) | 31708 | 2-Methoxy-4-methylamino-5-chlorobenzoic acid; 5-Chloro-2-methoxy-4-(methylamino)benzoic acid | C9H10ClNO3 | 详情 | 详情 |
Extended Information