2-Chloronicotinonitrile → tert-Butyl4-(3-cyano-2-pyridinyl)-1-piperazinecarboxylate

HRID 645667노트

반응식

HRID 645667 반응식
Cl[C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C(=O)([O-])O.[K+]>CN(C)C=O>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([C:2]2[C:3]([C:4]#[N:5])=[CH:6][CH:7]=[CH:8][N:9]=2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

참가 물질

5

반응물 3

HCID 810792-ChloronicotinonitrileHCID 143452tert-Butyl piperazine-1-carboxylateHCID 516893Potassium Bicarbonate

생성물 1

HCID 22061422tert-Butyl4-(3-cyano-2-pyridinyl)-1-piperazinecarboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

2-Chloro-nicotinonitrile (2.04 g, 14.7 mmol) was added to a mixture of piperazine-1-carboxylic acid tert-butyl ester (2.74 g, 14.7 mmol) and potassium hydrogencarbonate (1.77 g, 17.6 mmol) in N,N-dimethylformamide (45 mL). The mixture was heated at 90° C. overnight. The solvent was removed and residue was partitioned between ethyl acetate and water. The organic layer was washed with water and brine then dried over magnesium sulfate and filtered. The solvent was removed to give the titled compound as an oil. 1H-NMR (400 MHz, DMSO-d6) δ 8.428 (dd, 1H); 8.08 (dd 1H); 6.95 (dd, 1H); 3.58 (m, 4H); 3.47 (m, 4H); 1.42 (s, 9H).

후처리

  1. customThe solvent was removed
  2. customresidue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialthen dried over magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed

출처 및 근거

ORD 기록
ord-8b76c43a772a4f89aa7ba993427d3be0
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07704997B1

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