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

HRID 1504966노트

반응식

HRID 1504966 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 3007855Zincchloride촉매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6467590991534c90b83ac867d375a4e5
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216957B2

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