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【结 构 式】 
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【分子编号】30225 【品名】6-(3-[[1-(2-methylphenyl)-1H-imidazol-2-yl]sulfanyl]propoxy)-3,4-dihydro-2(1H)-quinolinone 【CA登记号】 |
【 分 子 式 】C22H23N3O2S 【 分 子 量 】393.50964 【元素组成】C 67.15% H 5.89% N 10.68% O 8.13% S 8.15% |
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)Alkylation of 2-mercapto-1-o-tolylimidazole (I) with the bromopropoxy tetrahydroquinolinone (II) in the presence of DBU gave sulfide (III). Then, asymmetric oxidation of (III) with cumene hydroperoxide and titanium tetraisopropoxide, using D-diethyl tartrate as the chiral auxiliary produced the target (S)-sulfoxide with low enantiomeric excess. Several recrystallizations from EtOH-EtOAc yielded the enantiomerically rich compound.
| 【1】 Nishi, T.; Chu, G.-N.; Okada, M.; Tamura, K.; Unemi, F.; Koga, Y.; Kido, M.; Igawa, T.; Ozeki, Y.; Uno, T.; Synthesis of 2(1H)-quinolinone derivatives and their inhibitory activity on the release of 12(S)-hydroxyeicosatetraenoic acid (12-HETE) from platelets. Chem Pharm Bull 1995, 43, 10, 1724. |
| 【2】 Nishi, T.; Uno, T.; Shu, Y.; Tamura, K.; Okada, M. (Otsuka Pharmaceutical Co., Ltd.); Carbostyril derivs.. EP 0651747; JP 1995033765; US 5541198; WO 9426732 . |
| 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) | 30223 | 1-(2-methylphenyl)-1H-imidazol-2-ylhydrosulfide; 1-(2-methylphenyl)-1H-imidazole-2-thiol | C10H10N2S | 详情 | 详情 | |
| (II) | 30224 | 6-(3-bromopropoxy)-3,4-dihydro-2(1H)-quinolinone | C12H14BrNO2 | 详情 | 详情 | |
| (III) | 30225 | 6-(3-[[1-(2-methylphenyl)-1H-imidazol-2-yl]sulfanyl]propoxy)-3,4-dihydro-2(1H)-quinolinone | C22H23N3O2S | 详情 | 详情 |
Extended Information