Sulfuric Acid → 4-amino-1-benzyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-one

HRID 639604Notes

Reaction equation

[CH2:1]([N:8]1[C:16]2[CH:15]=[C:14]([C:17]([F:20])([F:19])[F:18])[N:13]=[C:12]([NH:21]CC3C=CC=CC=3)[C:11]=2[NH:10][C:9]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OS(O)(=O)=O.C([O-])([O-])=O.[K+].[K+]>O>[NH2:21][C:12]1[C:11]2[NH:10][C:9](=[O:29])[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:16]=2[CH:15]=[C:14]([C:17]([F:20])([F:19])[F:18])[N:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1-Benzyl-4-benzylamino-6-trifluoromethyl-1,3-dihydro-imidazo[4,5-c]pyridine-2-one (2.63 g, 6.60 mmol) was dissolved in c.H2SO4 (50 ml) and the reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was cooled to 0° C. and ice was added. K2CO3 (150 g) was dissolved in water (700 ml) and the reaction mixture was added dropwise. The aqueous was extracted with EtOAc (6×500 ml). The combined organics were washed with brine (200 ml), dried over MgSO4 and concentrated in vacuo to give the title compound (1.20 g) as a white solid.

Workup

additionice was added
additionthe reaction mixture was added dropwise
extractionThe aqueous was extracted with EtOAc (6×500 ml)
washThe combined organics were washed with brine (200 ml)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-7e8137780a6043e899162e1b3ded48ed
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691877B2

Reaction notes

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