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 1775322ノート

反応式

HRID 1775322 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

(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%).

後処理

  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)

出典と根拠

ORDレコード
ord-fd0d4789dd9b4abb8269d7f1bd9a9429
出典データセット
uspto-grants-2016_02
特許番号
US09260441B2

反応ノート

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