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

HRID 1036236
ノート
印刷プレビュー

反応式

HRID 1036236 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]
参加物実験手順後処理出典と根拠反応ノート

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 6228
Dimethylformamide
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-f1011be5371d4221abbb9ca869876cb5
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08546396B2

反応ノート

読み込み中…

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