Ammonia → 5-(3H-Imidazo[4,5-c]pyridin-3-yl)-3-{1-[2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxamide

HRID 2391581Notes

Reaction equation

[N:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]([C:10]2[S:14][C:13]([C:15]([O:17]C)=O)=[C:12]([O:19][CH:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]([F:31])([F:30])[F:29])[CH3:21])[CH:11]=2)[CH:2]=1.[NH3:32]>CO>[N:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]([C:10]2[S:14][C:13]([C:15]([NH2:32])=[O:17])=[C:12]([O:19][CH:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]([F:29])([F:30])[F:31])[CH3:21])[CH:11]=2)[CH:2]=1

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of 92 mg of the above-synthesized methyl 5-(3H-imidazo[4,5-c]pyridin-3-yl)-3-{1-[2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxylate and 10 ml of a saturated solution of ammonia in methanol was stirred in a microwave vial at 125° C. for 4 h in the microwave cavity. The reaction mixture was allowed to come to room temperature, then another 10 ml of a saturated solution of ammonia in methanol were added and the procedure was repeated as described above. The solvent was removed under vacuum and the residue was purified by flash chromatography (n-hexane/ethyl acetate, elution gradient 10/0 to 3/7 (v/v)) to give the title compound.

Workup

customto come to room temperature
customThe solvent was removed under vacuum
customthe residue was purified by flash chromatography (n-hexane/ethyl acetate, elution gradient 10/0 to 3/7 (v/v))

Sources & evidence

ORD record: ord-816bdfe7c2db4622886d713e28af4354
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273890B2

Reaction notes

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