Ammonium formate → 3-cyclopropyl-6-(3,4-dimethoxyphenyl)-3H-imidazo[4,5-c]pyridin-4(5H)-one

HRID 2209009ノート

反応式

HRID 2209009 の反応式
C([O:8][C:9]1[C:14]2[N:15]([CH:18]3[CH2:20][CH2:19]3)[CH:16]=[N:17][C:13]=2[CH:12]=[C:11]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=2)[N:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CCO.CN(C=O)C.[OH-].[OH-].[Pd+2]>[CH:18]1([N:15]2[C:14]3[C:9](=[O:8])[NH:10][C:11]([C:21]4[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=4)=[CH:12][C:13]=3[N:17]=[CH:16]2)[CH2:19][CH2:20]1

参加物

6

反応物 2

HCID 2723923Ammonium formateHCID 1178428024-(benzyloxy)-3-cyclopropyl-6-(3,4-dimethoxyphenyl)-3H-imidazo[4,5-c]pyridine

生成物 1

HCID 1178434503-cyclopropyl-6-(3,4-dimethoxyphenyl)-3H-imidazo[4,5-c]pyridin-4(5H)-one

試薬・触媒・溶媒 3

HCID 9942167Palladium hydroxide触媒HCID 702Ethanol溶媒2 回HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
65 °C

実験手順

To a solution of 4-(benzyloxy)-3-cyclopropyl-6-(3,4-dimethoxyphenyl)-3H-imidazo[4,5-c]pyridine 2.36 (270 mg, 0.67 mmol) in EtOH (6.5 mL) and DMF (2.1 mL) was added ammonium formate (670 mg, 10.6 mmol) and Pd(OH)2 on carbon (20 wt. % Pd, 70 mg). The mixture was heated to 65° C. and stirred for 40 min. The mixture was diluted with DMF (10 mL) and EtOH (10 mL) and was filtered through Celite. The filtrate was concentrated in vacuo and the resulting crude solid was purified by silica gel chromatography (0% to 15% MeOH in DCM) to provide 3-cyclopropyl-6-(3,4-dimethoxyphenyl)-3H-imidazo[4,5-c]pyridin-4(5H)-one 2.37.

後処理

  1. filtrationwas filtered through Celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe resulting crude solid was purified by silica gel chromatography (0% to 15% MeOH in DCM)

出典と根拠

ORDレコード
ord-e26e229cb3a44a9b9dd38c155fafce57
出典データセット
uspto-grants-2016_06
特許番号
US09376441B2

反応ノート

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