Ammonia → 5-{[6-(Methylsulfonyl)pyridin-3-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carboxamide
반응식
[CH3:1][S:2]([C:5]1[N:10]=[CH:9][C:8]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[C:19]([O:21][CH:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:20]=2)[NH:17][C:16]([C:28]([OH:30])=O)=[CH:15]3)=[CH:7][CH:6]=1)(=[O:4])=[O:3].O.O[N:33]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.N.Cl>CN(C)C=O>[CH3:1][S:2]([C:5]1[N:10]=[CH:9][C:8]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[C:19]([O:21][CH:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:20]=2)[NH:17][C:16]([C:28]([NH2:33])=[O:30])=[CH:15]3)=[CH:7][CH:6]=1)(=[O:3])=[O:4]참가 물질
반응물 5
생성물 1
시약·촉매·용매 1
실험 절차
To a solution of 5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indole-2-carboxylic acid (3 g) in N,N-dimethylformamide (20 mL) were added 1-hydroxybenzotriazole monohydrate (1.6 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2 g), and 10% aqueous ammonia (27 mL), and the mixture was stirred at room temperature for 1 hr. 1N HCl was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained crude product was crystallized from diethyl ether to give the title compound (1.35 g, yield 45%) as yellow powder.
후처리
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe obtained crude product
- customwas crystallized from diethyl ether
출처 및 근거
- ORD 기록
- ord-bffa31973c164cc0aee002d60ce70e3c
- 출처 데이터셋
- uspto-grants-2013_10
- 특허 번호
- US08557805B2
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