Isoniazid → 3-pyridin-4-yl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazole

HRID 2102293

반응식

HRID 2102293 반응식
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=O.[C:7]([NH:15][NH2:16])(=O)[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1>C(Cl)Cl>[N:11]1[CH:12]=[CH:13][C:8]([C:7]2[N:1]3[CH2:5][CH2:4][CH2:3][C:2]3=[N:16][N:15]=2)=[CH:9][CH:10]=1

참가 물질

4

반응물 2

HCID 3767IsoniazidHCID 120252-Pyrrolidone

생성물 1

HCID 8531463-pyridin-4-yl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazole수율 11%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
120 °C

실험 절차

Me3OBF4 (2.66 g, 18 mmol) was added to a solution of 2-pyrollidinone in DCM (150 ml) and the reaction mixture was stirred for 24 h. The reaction mixture was washed with aq. sat. NaHCO3, dried and concentrated. The residue was dissolved in EtOH (4 ml) and isonicotinic hydrazide (1.37 g, 10 mmol) was added. The mixture was heated in a microwave reactor for 1 h at 120° C. The volatiles were removed and the crude product purified with column chromatography (DCM/MeOH 20:1) to give 319 mg (11%) of the title compound. 1H NMR: 2.87 (m, 2H), 3.05 (t, 2H), 4.28 (t, 2H), 7.72 (d,2H), 8.72 (d, 2H).

후처리

  1. washThe reaction mixture was washed with aq. sat. NaHCO3
  2. customdried
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in EtOH (4 ml)
  5. customThe volatiles were removed
  6. customthe crude product purified with column chromatography (DCM/MeOH 20:1)

출처 및 근거

ORD 기록
ord-abaf5ea9dffc43dba276908e4574fe5c
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576077B2

연결된 노트

불러오는 중…