Oxalyl chloride → Ethyl 5-methylamino-2-[4-[(E)-4,4,4-trifluorobut-2-enoyl]piperazin-1-yl]thiazole-4-carboxylate
反応式
[F:1][C:2]([F:9])([F:8])/[CH:3]=[CH:4]/[C:5](O)=[O:6].C(Cl)(=O)C(Cl)=O.Cl.[CH3:17][NH:18][C:19]1[S:23][C:22]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[N:21][C:20]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31].CCN(C(C)C)C(C)C>ClCCl.CN(C=O)C>[CH3:17][NH:18][C:19]1[S:23][C:22]([N:24]2[CH2:29][CH2:28][N:27]([C:5](=[O:6])/[CH:4]=[CH:3]/[C:2]([F:9])([F:8])[F:1])[CH2:26][CH2:25]2)=[N:21][C:20]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31]参加物
7
反応物 4
生成物 1
試薬・触媒・溶媒 2
実験手順
(E)-4,4,4-Trifluorobut-2-enoic acid (25 mg, 0.18 mmol) was dissolved in dichloromethane (1 ml), oxalyl chloride (16 μl, 0.18 mol) and one drop of DMF were added and the resulting solution was stirred at room temperature for 10 minutes. This solution was added to a solution of ethyl 5-methylamino-2-piperazin-1-yl-thiazole-4-carboxylate hydrochloride (41 mg, 0.15 mmol) and DIPEA (79 μl, 0.45 mmol) in anhydrous DCM (2 ml) and the resulting mixture was stirred at room temperature overnight. The mixture was concentrated under reduced pressure and the resulting residue was purified by preparative HPLC (Waters Xbridge, gradient of water containing 0.1% NH3 and acetonitrile) to yield 7 mg of a solid (0.017 mmol, 11%).
後処理
- stirringthe resulting mixture was stirred at room temperature overnight
- concentrationThe mixture was concentrated under reduced pressure
- customthe resulting residue was purified by preparative HPLC (Waters Xbridge, gradient of water containing 0.1% NH3 and acetonitrile)
出典と根拠
- ORDレコード
- ord-072eddde2ba648c79edd065030207a0f
- 出典データセット
- uspto-grants-2016_02
- 特許番号
- US09260441B2
反応ノート
読み込み中…