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

HRID 2209009노트

반응식

HRID 2209009 반응식
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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 9942167Palladium hydroxide촉매HCID 702Ethanol용매2회HCID 6228Dimethylformamide용매2회

반응 조건

온도
65 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e26e229cb3a44a9b9dd38c155fafce57
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376441B2

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