Tetrahydrofuran → 4-methyl-1-(2-(1-methyl-1H-indazol-5-ylamino)pyrimidin-4-yl)-1H-pyrrole-3-carbaldehyde
反応式
[CH3:1][C:2]1[C:6]([CH:7]=[O:8])=[CH:5][NH:4]N=1.[CH3:9][N:10]1[C:18]2[C:13](=[CH:14][C:15]([NH:19][C:20]3[N:25]=[C:24](S(C)(=O)=O)[CH:23]=[CH:22][N:21]=3)=[CH:16][CH:17]=2)[CH:12]=[N:11]1.[H-].[Na+].[CH2:32]1COCC1>>[CH3:1][C:2]1[C:6]([CH:7]=[O:8])=[CH:5][N:4]([C:24]2[CH:23]=[CH:22][N:21]=[C:20]([NH:19][C:15]3[CH:14]=[C:13]4[C:18](=[CH:17][CH:16]=3)[N:10]([CH3:9])[N:11]=[CH:12]4)[N:25]=2)[CH:32]=1参加物
実験手順
To a solution of 3-methyl-1H-pyrazole-4-carbaldehyde, intermediate 12 (0.33 g, 3.0 mmol) in 10 mL of THF was added 0.12 g of 60% sodium hydride with ice bath cooling and then it was stirred for 20 minute at the same temperature. To this, was added of 10 mL solution of 1-methyl-N-(4-(methansulfonyl)pyrimidin-2-yl)-1H-indazol-5-amine (0.6 g, 2.0 mmol) in THF. The reaction was allowed to warm up to room temperature and then stirred for 2 hours at rt. The reaction was quenched with water, extracted with dichloromethane (×2) and washed with brine. The collected organic layers were dried over anhydrous sodium sulfate and then concentrated in vacuo. The resulting residue was solidified with heptane and then collected by filtration to afford the desired intermediate 13 as a white solid (0.45 g, 66%).
後処理
- temperaturecooling
- stirringstirred for 2 hours at rt
- customThe reaction was quenched with water
- extractionextracted with dichloromethane (×2)
- washwashed with brine
- dry with materialThe collected organic layers were dried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
- filtrationcollected by filtration
出典と根拠
- ORDレコード
- ord-160bc66f1f5e47c18bb3fcae70a9e27a
- 出典データセット
- uspto-grants-2014_10
- 特許番号
- US08871778B2
反応ノート
読み込み中…