Dimethylformamide → Rac-cis-tert-butyl 4-(2-{2-[(6-cyano-2-methylpyrimidin-4-yl)(4-methoxybenzyl)amino]ethyl}cyclopropyl)piperidine-1-carboxylate
反応式
I[CH2:2][CH2:3][C@H:4]1[CH2:6][C@H:5]1[CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1.[OH:20][C:21]1[CH:37]=[CH:36][C:24]([CH2:25][NH:26][C:27]2[N:32]=[C:31]([CH3:33])[N:30]=[C:29]([C:34]#[N:35])[CH:28]=2)=[CH:23][CH:22]=1.[H-].[Na+].[CH3:40]N(C=O)C>>[C:34]([C:29]1[N:30]=[C:31]([CH3:33])[N:32]=[C:27]([N:26]([CH2:25][C:24]2[CH:23]=[CH:22][C:21]([O:20][CH3:40])=[CH:37][CH:36]=2)[CH2:2][CH2:3][C@H:4]2[CH2:6][C@H:5]2[CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[CH:28]=1)#[N:35]参加物
5
反応物 4
生成物 1
実験手順
Rac-cis-tert-butyl 4-[2-(2-iodoethyl)cyclopropyl]piperidine-1-carboxylate (86 mg, 0.23 mmol) from Step 3 of this example and 6-[(4-hydroxybenzyl)amino]-2-methylpyrimidine-4-carbonitrile (63.4 mg, 0.25 mmol) from Step 2 of this example were dissolved in DMF (2.3 mL), sodium hydride (18 mg, 0.45 mmol) was added. After 10 minutes, the reaction was quenched with saturated ammonia chloride solution (5 mL), extracted with ethyl acetate (10 mL), second washed with brine (5 mL). The organic phase was dried by magnesium sulfate, filtered, concentrated and purified by preparative-TLC (Analtech Silica Gel GF 1500 μM, 20×20 cm) using 30% ethyl acetate/hexane to give the title compound as a white solid.
後処理
- customthe reaction was quenched with saturated ammonia chloride solution (5 mL)
- extractionextracted with ethyl acetate (10 mL)
- washsecond washed with brine (5 mL)
- dry with materialThe organic phase was dried by magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- custompurified by preparative-TLC (Analtech Silica Gel GF 1500 μM, 20×20 cm)
出典と根拠
- ORDレコード
- ord-71173aacc13d495db7d2958e92b42851
- 出典データセット
- uspto-grants-2013_10
- 特許番号
- US08552022B2
反応ノート
読み込み中…