Potassium Carbonate → N-pentyl-5-(3-phenyl-1H-1,2,4-triazol-5-yl)-1H-imidazol-4-amine

HRID 249774ノート

反応式

HRID 249774 の反応式
[CH2:1]([NH:6][C:7]1[N:8]=[CH:9][NH:10][C:11]=1[C:12]#[N:13])[CH2:2][CH2:3][CH2:4][CH3:5].[C:14]([NH:22][NH2:23])(=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)CCC.O>[CH2:1]([NH:6][C:7]1[N:8]=[CH:9][NH:10][C:11]=1[C:12]1[NH:23][N:22]=[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:13]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 11955BenzoylhydrazineHCID 451205654-(pentylamino)-1H-imidazole-5-carbonitrile

生成物 1

HCID 135984693N-pentyl-5-(3-phenyl-1H-1,2,4-triazol-5-yl)-1H-imidazol-4-amine収率 17%

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 962Water溶媒

反応条件

温度
170 °C

実験手順

The mixture of 4-(pentylamino)-1H-imidazole-5-carbonitrile (200 mg, 1.12 mmol), benzhydrazide (229 mg, 1.68 mmol) and potassium carbonate (100 mg, 0.72 mmol) in 1-butanol (6 ml) in a sealed tube was stirred at 170° C. for 14 hours. The reaction was diluted with water and extracted with EtOAc three times. The combined organic layers was dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by preparative LCMS (method A) to yield the desired product (50 mg, 17% yield). LCMS calculated for C16H21N6 (M+H): 297.2. found 297.1.

後処理

  1. extractionextracted with EtOAc three times
  2. dry with materialThe combined organic layers was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by preparative LCMS (method A)

出典と根拠

ORDレコード
ord-bd97f9f18896437e892f53f931c7c930
出典データセット
uspto-grants-2011_01
特許番号
US07863285B2

反応ノート

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