Oxalyl chloride → (E)-4,4-Difluoro-1-[4-(5-methyl-1,2,4-oxadiazol-3-yl)piperazin-1-yl]pent-2-en-1-one

HRID 1775322노트

반응식

HRID 1775322 반응식
[F:1][C:2]([F:11])([CH:8](F)F)/[CH:3]=[CH:4]/[C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.Cl.[CH3:19][C:20]1[O:24][N:23]=[C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[N:21]=1>ClCCl.CN(C=O)C>[F:11][C:2]([F:1])([CH3:8])/[CH:3]=[CH:4]/[C:5]([N:28]1[CH2:29][CH2:30][N:25]([C:22]2[N:21]=[C:20]([CH3:19])[O:24][N:23]=2)[CH2:26][CH2:27]1)=[O:7]

참가 물질

6

반응물 3

HCID 65578Oxalyl chlorideHCID 866860471-(5-Methyl-1,2,4-oxadiazol-3-yl)piperazine hydrochlorideHCID 86691165(E)-4,4,5,5-tetrafluoropent-2-enoic acid

생성물 1

HCID 71765252(E)-4,4-Difluoro-1-[4-(5-methyl-1,2,4-oxadiazol-3-yl)piperazin-1-yl]pent-2-en-1-one수율 69%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매2회

실험 절차

(E)-4,4,5,5-Tetrafluoropent-2-enoic acid (31 mg, 0.23 mmol) was dissolved in dichloromethane (1 ml), oxalyl chloride (20 μl, 0.23 mol) and one drop of DMF were added and the resulting solution was stirred at room temperature for 15 minutes. This solution was added to a solution of 5-methyl-3-piperazin-1-yl-1,2,4-oxadiazole hydrochloride (25 mg, 0.122 mmol) in dichloromethane (2 ml) and the resulting mixture was stirred at room temperature for three hours. The solvent was removed 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 24.3 mg of a solid (0.083 mmol, 69%).

후처리

  1. stirringthe resulting mixture was stirred at room temperature for three hours
  2. customThe solvent was removed under reduced pressure
  3. 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-fd0d4789dd9b4abb8269d7f1bd9a9429
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260441B2

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