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

HRID 2102293

反応式

HRID 2102293 の反応式
[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

参加物

4

反応物 2

HCID 3767IsoniazidHCID 120252-Pyrrolidone

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
120 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-abaf5ea9dffc43dba276908e4574fe5c
出典データセット
uspto-grants-2009_08
特許番号
US07576077B2

関連ノート

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