Ammonia → 5-(1H-imidazo[4,5-c]pyridin-1-yl)-3-{[2-(trifluoromethoxy)benzyl]oxy}thiophene-2-carboxamide

HRID 2391600Notes

Reaction equation

[N:1]1([C:10]2[S:14][C:13]([C:15]([O:17]C)=O)=[C:12]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][C:28]([F:31])([F:30])[F:29])[CH:11]=2)[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.[NH3:32]>CO>[N:1]1([C:10]2[S:14][C:13]([C:15]([NH2:32])=[O:17])=[C:12]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][C:28]([F:30])([F:31])[F:29])[CH:11]=2)[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of 26.8 mg of methyl 5-(1H-imidazo[4,5-c]pyridin-1-yl)-3-{[2-(trifluoromethoxy)benzyl]oxy}thiophene-2-carboxylate and 5 ml of a saturated solution of ammonia in methanol is stirred in a microwave vial at 125° C. for 4 h in the microwave cavity. The reaction mixture is concentrated to dryness, the resulting residue is dissolved in ethyl acetate and purified by flash chromatography [Silica gel, eluent: ethyl acetate/methanol, elution gradient of 100/0 (v/v) to 95/5 (v/v)] to yield the title compound.

Workup

concentrationThe reaction mixture is concentrated to dryness
dissolutionthe resulting residue is dissolved in ethyl acetate
custompurified by flash chromatography [Silica gel, eluent: ethyl acetate/methanol, elution gradient of 100/0 (v/v) to 95/5 (v/v)]

Sources & evidence

ORD record: ord-9e8e0be31ce64ecc8dc0e4532c1ce506
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273890B2

Reaction notes

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