N-[(4-methoxyphenyl)methyl]-1,3-thiazol-2-amine → 4-Chloro-N-(4-methoxybenzyl)-N-(thiazol-2-YL)quinoline-7-sulfonamide
반응식
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][NH:8][C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=[CH:5][CH:4]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Cl:26][C:27]1[C:36]2[C:31](=[CH:32][C:33]([S:37](OC3C(F)=C(F)C(F)=C(F)C=3F)(=[O:39])=[O:38])=[CH:34][CH:35]=2)[N:30]=[CH:29][CH:28]=1>C1COCC1>[Cl:26][C:27]1[C:36]2[C:31](=[CH:32][C:33]([S:37]([N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:15][CH:14]=3)[C:9]3[S:10][CH:11]=[CH:12][N:13]=3)(=[O:38])=[O:39])=[CH:34][CH:35]=2)[N:30]=[CH:29][CH:28]=1참가 물질
반응 조건
- 온도
- -78 °C
실험 절차
A solution of N-(4-methoxybenzyl)thiazol-2-amine (0.306 g, 1.389 mmol) in THF (5.29 ml) was cooled to −78° C. for 10 minutes, and lithium bis(trimethylsilyl)amide (1.0M solution in THF) (1.323 ml, 1.323 mmol) was added drop wise. The cold bath was removed for 5 minutes, and then the reaction vessel was re-cooled to −78° C. for 10 minutes. A solution of perfluorophenyl 4-chloroquinoline-7-sulfonate (0.542 g, 1.323 mmol) in THF (2.65 ml, 1.323 mmol) was added drop wise, and the reaction was stirred for 15 minutes until complete conversion to the desired product. After warming to RT, the reaction was quenched with sat. aq ammonium chloride solution, diluted with EtOAc (5 mL) and washed with water (10 mL×2). The combined organics were dried over sodium sulfate, filtered and concentrated. The material was then purified via silica gel chromatography (40-g column) eluting with 0 to 100% ethyl acetate in heptanes, to yield 4-chloro-N-(4-methoxybenzyl)-N-(thiazol-2-yl)quinoline-7-sulfonamide (0.481 g, 1.079 mmol, 82% yield) as a white solid. m/z (ESI) 446.1 (M+H)+.
후처리
- customThe cold bath was removed for 5 minutes
출처 및 근거
- ORD 기록
- ord-27a55f1269194e4ab91f183b25a3321f
- 출처 데이터셋
- uspto-grants-2015_04
- 특허 번호
- US09012443B2
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