Dimethylformamide → 6-[(3-[1,3]Dioxolan-2-yl-propoxy)]-N-[4-(5-cyano-3-pyridin-3yl-pyrazol-1-yl)phenyl]nicotinamide
反応式
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]=1参加物
5
反応物 4
生成物 1
反応条件
- 温度
- 65 °C
実験手順
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%).
後処理
- 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
出典と根拠
- ORDレコード
- ord-90e72c90bb8b4cb9bd67d351b0631128
- 出典データセット
- uspto-grants-2003_01
- 特許番号
- US06506747B1
反応ノート
読み込み中…