Oxalyl chloride → Ethyl 5-methylamino-2-[4-[(E)-4,4,4-trifluorobut-2-enoyl]piperazin-1-yl]thiazole-4-carboxylate
반응식
[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]참가 물질
7
반응물 4
생성물 1
시약·촉매·용매 2
실험 절차
(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%).
후처리
- 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)
출처 및 근거
- ORD 기록
- ord-072eddde2ba648c79edd065030207a0f
- 출처 데이터셋
- uspto-grants-2016_02
- 특허 번호
- US09260441B2
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