1,2-Dichloroethane → Methyl 3-[(methylamino)carbonyl]-5-(5-methylpyridin-2-yl)benzoate
반응식
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][N:15]=2)[CH:13]=1)[C:8](O)=[O:9])=[O:4].N.O1CCOCC1.C(Cl)CCl.C1C=CC2N(O)N=[N:38][C:36]=2C=1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH3:36][NH:38][C:8]([C:7]1[CH:6]=[C:5]([CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][N:15]=2)[CH:11]=1)[C:3]([O:2][CH3:1])=[O:4])=[O:9]참가 물질
8
반응물 6
생성물 1
시약·촉매·용매 1
실험 절차
To a solution of 3-(methoxycarbonyl)-5-(5-methylpyridin-2-yl)benzoic acid (1.85 g, 6.82 mmol) in N,N-dimethylformamide (20 mL) was added 2 M ammonia in dioxane (10.2 mL, 20.4 mmol), EDC (2.61 g, 13.6 mmol), HOBT (2.09 g, 13.6 mmol) and N,N-diisopropylethylamine (4.76 mL, 27.3 mmol). After 16 h, the reaction was concentrated and the residue was dissolved in 200 ml of dichloromethane. The mixture was washed with 100 mL of saturated aqueous sodium bicarbonate solution (2×) and brine (100 ml). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (1% ethyl acetate/hexane→60% ethyl acetate/hexane) to give the title compound (1.82 g). MS 285.1 (M+1).
후처리
- concentrationthe reaction was concentrated
- dissolutionthe residue was dissolved in 200 ml of dichloromethane
- washThe mixture was washed with 100 mL of saturated aqueous sodium bicarbonate solution (2×) and brine (100 ml)
- dry with materialThe combined organic extracts were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by silica gel chromatography (1% ethyl acetate/hexane→60% ethyl acetate/hexane)
출처 및 근거
- ORD 기록
- ord-56d7b4349c594464979d9dc1d0a41253
- 출처 데이터셋
- uspto-grants-2012_08
- 특허 번호
- US08247401B2
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