Dimethylacetamide → 4-(4-fluorophenyl)-7-(((2S)-2-methyl-5-(trifluoromethyl)piperazin-1-yl)methyl)quinoline-2-carbonitrile

HRID 922785노트

반응식

HRID 922785 반응식
[CH3:1][C@H:2]1[CH2:7][NH:6][CH:5]([C:8]([F:11])([F:10])[F:9])[CH2:4][NH:3]1.CC(N(C)C)=O.CCN(C(C)C)C(C)C.Br[CH2:28][C:29]1[CH:38]=[C:37]2[C:32]([C:33]([C:41]3[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=3)=[CH:34][C:35]([C:39]#[N:40])=[N:36]2)=[CH:31][CH:30]=1>CCOC(C)=O>[F:47][C:44]1[CH:45]=[CH:46][C:41]([C:33]2[C:32]3[C:37](=[CH:38][C:29]([CH2:28][N:3]4[CH2:4][CH:5]([C:8]([F:11])([F:9])[F:10])[NH:6][CH2:7][C@@H:2]4[CH3:1])=[CH:30][CH:31]=3)[N:36]=[C:35]([C:39]#[N:40])[CH:34]=2)=[CH:42][CH:43]=1

참가 물질

6

반응물 4

HCID 31374DimethylacetamideHCID 81531DiisopropylethylamineHCID 194270117-(Bromomethyl)-4-(4-fluorophenyl)quinoline-2-carbonitrileHCID 89543685(2S)-2-methyl-5-(trifluoromethyl)piperazine

생성물 1

HCID 895548164-(4-fluorophenyl)-7-(((2S)-2-methyl-5-(trifluoromethyl)piperazin-1-yl)methyl)quinoline-2-carbonitrile

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

To the solution of (2S)-2-methyl-5-(trifluoromethyl)piperazine (4-20) was added DMA (1.76 ml), DIEA (0.614 ml, 3.52 mmol) followed by 7-(bromomethyl)-4-(4-fluorophenyl)quinoline-2-carbonitrile (300 mg, 0.879 mmol). The reaction was heated to 50° C. for 4 hours. The reaction was diluted with EtOAc and then washed with H2O, brine, dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica gel eluting with hexanes to EtOAc to provide 4-(4-fluorophenyl)-7-(((2S)-2-methyl-5-(trifluoromethyl)piperazin-1-yl)methyl)quinoline-2-carbonitrile as a colorless solid. LRMS m/z (M+H)+ 429.2 found, 429.4 required.

후처리

  1. washwashed with H2O, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica gel eluting with hexanes to EtOAc

출처 및 근거

ORD 기록
ord-e5c5b617b3e14df39dfe813d851feac0
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278960B2

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