Dimethylformamide → 6-[(3-[1,3]Dioxolan-2-yl-propoxy)]-N-[4-(5-cyano-3-pyridin-3yl-pyrazol-1-yl)phenyl]nicotinamide
반응식
C(CCCOC1C=[CH:33][C:10]([C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[C:24]([C:25]#[N:26])=[CH:23][C:22]([C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)=[N:21]3)=[CH:16][CH:15]=2)=[O:12])=[CH:9][CH:8]=1)#N.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:42][CH2:43][CH2:44][CH:45]1[O:49][CH2:48][CH2:47][O:46]1.C[N:51]([CH:53]=[O:54])C>>[O:46]1[CH2:47][CH2:48][O:49][CH:45]1[CH2:44][CH2:43][CH2:42][O:54][C:53]1[CH:8]=[CH:9][C:10]([C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([N:20]3[C:24]([C:25]#[N:26])=[CH:23][C:22]([C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)=[N:21]3)=[CH:18][CH:19]=2)=[O:12])=[CH:33][N:51]=1참가 물질
5
반응물 4
생성물 1
반응 조건
- 온도
- 65 °C
실험 절차
To a stirred solution of 6-hydroxynicotinic acid methyl ester (prepared as describrd in Example 25) (10 mmol) in DMF (30 mL) was added cesium carbonate (10 mmol). After 30 minutes, 2-(3-chloropropyl)-1,3-dioxolane (10 mmol) was added and the reaction mixture was heated at 65° C. on an oil bath. After 2 days, the mixture was cooled to room temperature, volatiles were removed, the residue was taken up in water, and extracted with dichloromethane. The organic phase was dried over magnesium sulfate and concentrated. Chromatography of the residue over silica gel (eluent dichloromethane/ethyl acetate 9:1) gave the desired product as the faster eluting product (311 mg, 12%).
후처리
- waitAfter 2 days
- temperaturethe mixture was cooled to room temperature
- customvolatiles were removed
- extractionextracted with dichloromethane
- dry with materialThe organic phase was dried over magnesium sulfate
- concentrationconcentrated
출처 및 근거
- ORD 기록
- ord-90e72c90bb8b4cb9bd67d351b0631128
- 출처 데이터셋
- uspto-grants-2003_01
- 특허 번호
- US06506747B1
반응 노트
불러오는 중…