(3-Amino-2-benzylamino-6-trifluormethyl-pyridin-4-yl)-carbamic acid ethyl ester → 4-Benzylamino-6-trifluoromethyl-1,3-dihydro-imidazo(4,5-c)pyridine-2-one

HRID 639632Notes

Reaction equation

C([O:3][C:4](=O)[NH:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:9]=[C:8]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:7]=1[NH2:24])C>C(O)(=O)C>[CH2:17]([NH:16][C:8]1[C:7]2[NH:24][C:4](=[O:3])[NH:5][C:6]=2[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:9]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 80 °C

Procedure

(3-amino-2-benzylamino-6-trifluormethyl-pyridin-4-yl)-carbamic acid ethyl ester (88 mg, 0.25 mmol) was dissolved in 5 mL of acetic acid and the reaction mixture was stirred at 80° C. overnight. The solvent was removed and the gum was partitioned in water/ethyl acetate. The organic layer was isolated, dried over MgSO4, the solvent was removed in vacuo and purified by column chromatography on silica eluting with a gradient of 1% to 5% of methanol in ethyl acetate to give 37 mg of the title compound as a colourless gum.

Workup

customThe solvent was removed
customthe gum was partitioned in water/ethyl acetate
customThe organic layer was isolated
dry with materialdried over MgSO4
customthe solvent was removed in vacuo
custompurified by column chromatography on silica eluting with a gradient of 1% to 5% of methanol in ethyl acetate

Sources & evidence

ORD record: ord-22f43b8b151f45279b93b5529ce0ad53
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691877B2

Reaction notes

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