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

HRID 592194ノート

反応式

HRID 592194 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.[N:30]#[C:31]Br.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C: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:30]

参加物

6

反応物 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 584476702-(4-(2-methylpyridin-4-yl)phenyl)-N-(5-(piperazin-1-yl)pyridin-2-yl)acetamide

生成物 1

HCID 58447785N-(5-(4-cyanopiperazin-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), Cyanogen Bromide (13 mg, 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-cyanopiperazin-1-yl)pyridin-2-yl)-2-(4-(2-methylpyridin-4-yl)phenyl)acetamide 176. MS m/z 413.2 (M+1); 1H NMR 400 MHz (MeOD) δ 8.39(d, 1 Hz), 7.96(s, 1H), 7.89(d, 1H),7.68(d, 2H), 7.58(s, 1H), 7.50(d, 1H), 7.46(d, 2H), 7.37(dd, 1H), 3.74(s, 2H), 3.35(t, 4H), 3.18(t, 4H),2.55(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-0164661f9b2549fc82adc1bbf5655aa7
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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