Acetone → 4-(5-((2-Cyanopropan-2-yl)amino)pyridin-2-yl)butanenitrile

HRID 1504966ノート

反応式

HRID 1504966 の反応式
[Si]([C:5]#[N:6])(C)(C)C.[NH2:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][C:17]#[N:18])=[N:12][CH:13]=1.[CH3:19][C:20]([CH3:22])=O>[Cl-].[Cl-].[Zn+2]>[C:5]([C:20]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][C:17]#[N:18])=[N:12][CH:13]=1)([CH3:22])[CH3:19])#[N:6]

参加物

5

反応物 3

HCID 180AcetoneHCID 82115Trimethylsilyl cyanideHCID 682926344-(5-Aminopyridin-2-yl)butanenitrile

生成物 1

HCID 682923294-(5-((2-Cyanopropan-2-yl)amino)pyridin-2-yl)butanenitrile収率 102.2%

試薬・触媒・溶媒 1

HCID 3007855Zincchloride触媒

実験手順

TMSCN (0.24 mL, 1.8 mmol) was added to a mixture of compound 78 (100 mg, 0.6 mmol), acetone (0.27 mL, 3.6 mmol) and ZnCl2 (10 mg, 0.08 mmol) with stirring. The reaction mixture was stirred at room temperature for 1 h and concentrated in vacuo. The residue was diluted with water and extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated to dryness to give compound 79 (140 mg, 98%) as a light yellow oil. The crude product was used directly for the next step without purification. 1H NMR (400 MHz, CDCl3) δ8.12 (s, 1H), 7.20-7.25 (m, 1H), 7.00-7.06 (m, 1H), 2.81 (t, 2H, J=7.1 Hz). 2.32 (t, 2H, J=7.1 Hz), 1.98-2.12 (m, 2H), 1.69 (s, 6H).

後処理

  1. stirringThe reaction mixture was stirred at room temperature for 1 h
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with DCM
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-6467590991534c90b83ac867d375a4e5
出典データセット
uspto-grants-2015_12
特許番号
US09216957B2

反応ノート

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