Water → N-(5-(4-(cyanomethyl)piperazin-1-yl)pyridin-2-yl)-2-(4-(2-methylpyridin-4-yl)phenyl)acetamide

HRID 592193ノート

反応式

HRID 592193 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([N:24]4[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]4)=[CH:20][N:19]=3)=[O:16])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.Br[CH2:31][C:32]#[N:33].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C:32]([CH2:31][N:27]1[CH2:28][CH2:29][N:24]([C:21]2[CH:22]=[CH:23][C:18]([NH:17][C:15](=[O:16])[CH2:14][C:11]3[CH:12]=[CH:13][C:8]([C:6]4[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=4)=[CH:9][CH:10]=3)=[N:19][CH:20]=2)[CH2:25][CH2:26]1)#[N:33]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 584476702-(4-(2-methylpyridin-4-yl)phenyl)-N-(5-(piperazin-1-yl)pyridin-2-yl)acetamide

生成物 1

HCID 58447747N-(5-(4-(cyanomethyl)piperazin-1-yl)pyridin-2-yl)-2-(4-(2-methylpyridin-4-yl)phenyl)acetamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 2-(4-(2-methylpyridin-4-yl)phenyl)-N-(5-(piperazin-1-yl)pyridin-2-yl)acetamide 131-1 (39 mg, 0.10 mmol), 2-bromoacetonitrile (8 uL, 0.12 mmol) and Potassium Carbonate (28 mg, 0.20 mmol) in DMF (1 mL) was stirred at room temperature overnight. The mixture was poured into water (5 ml) and extracted with ethyl acetate (5 mL×3). The combined organic phases were dried over Na2SO4 and concentrated. The crude product was purified by reverse phase HPLC to give N-(5-(4-(cyanomethyl)piperazin-1-yl)pyridin-2-yl)-2-(4-(2-methylpyridin-4-yl)phenyl)acetamide 175. MS m/z 427.2 (M+1); 1H NMR 400 MHz (MeOD) δ 8.37(d, 1H), 7.94(s, 1H), 7.87(d, 1H), 7.68(d, 2H), 7.55(s, 1H), 7.48-7.44(m, 3H), 7.36(dd, 1H), 3.74(s, 2H), 3.67(s, 2H), 3.17(t, 4H), 2.69(t, 4H), 2.54(s, 3H).

後処理

  1. extractionextracted with ethyl acetate (5 mL×3)
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude product was purified by reverse phase HPLC

出典と根拠

ORDレコード
ord-0ee08a7ba0a44948b86d4a06522d19d3
出典データセット
uspto-grants-2016_01
特許番号
US09238646B2

反応ノート

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