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

HRID 922785ノート

反応式

HRID 922785 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e5c5b617b3e14df39dfe813d851feac0
出典データセット
uspto-grants-2016_03
特許番号
US09278960B2

反応ノート

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