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【结 构 式】 
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【分子编号】44386 【品名】N'-[(3S,4aS,10aR)-6-methoxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-3-yl]-N,N-diethylsulfamide 【CA登记号】 |
【 分 子 式 】C21H35N3O3S 【 分 子 量 】409.59332 【元素组成】C 61.58% H 8.61% N 10.26% O 11.72% S 7.83% |
合成路线1
该中间体在本合成路线中的序号：(XVII)Free NH group of (XI) is alkylated by reductocondensation with propionaldehyde (XII) and H2 over Pd/C, giving the N-propyl derivative (XIII). The reaction of the ester group of (XIII) with hydrazine yields the corresponding hydrazide (XIV), which is submitted to degradation with nitrosyl chloride in THF to afford the amine (XV). The condensation of (XV) with N,N-diethylsulfamoyl chloride (XVI) by means of TEA in chloroform gives the sulfamide (XVII), which is finally demethylated by a treatment with BBr3 in dichloromethane.
| 【1】 Nordmann, R.; Petcher, T.J.; Octahydrobenzo[g]quinolines: Potent dopamine agonists which show the relationship between ergolines and apomorphine. J Med Chem 1985, 28, 3, 367. |
| 【2】 Petcher, T.J.; Nordmann, R. (Novartis AG); Novel pharmaceutically active 1,2,3,4,4a,5,10,10a-octahydrobenzo(g)quinoline derivs.. EP 0077754; ES 8606281; ES 8706120 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XI) | 44381 | methyl (3S,4aR,10aR)-6-methoxy-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-3-carboxylate | C16H21NO3 | 详情 | 详情 | |
| (XII) | 15966 | propionaldehyde | 123-38-6 | C3H6O | 详情 | 详情 |
| (XIII) | 44382 | methyl (3S,4aR,10aR)-6-methoxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-3-carboxylate | C19H27NO3 | 详情 | 详情 | |
| (XIV) | 44383 | (3S,4aR,10aR)-6-methoxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-3-carbohydrazide | C18H27N3O2 | 详情 | 详情 | |
| (XV) | 44384 | (3S,4aS,10aR)-6-methoxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-3-ylamine; (3S,4aS,10aR)-6-methoxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-3-amine | C17H26N2O | 详情 | 详情 | |
| (XVI) | 44385 | 1-[(chlorosulfonyl)(ethyl)amino]ethane | C4H10ClNO2S | 详情 | 详情 | |
| (XVII) | 44386 | N'-[(3S,4aS,10aR)-6-methoxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-3-yl]-N,N-diethylsulfamide | C21H35N3O3S | 详情 | 详情 |