Ammonia → 3-[1-(2-Chlorophenyl)ethoxy]-5-(3H-imidazo[4,5-c]pyridin-3-yl)thio-phene-2-carboxamide

HRID 2391579Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:10][C:11]1[CH:15]=[C:14]([N:16]2[C:20]3[CH:21]=[N:22][CH:23]=[CH:24][C:19]=3[N:18]=[CH:17]2)[S:13][C:12]=1[C:25]([O:27]C)=O)[CH3:9].[NH3:29]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:10][C:11]1[CH:15]=[C:14]([N:16]2[C:20]3[CH:21]=[N:22][CH:23]=[CH:24][C:19]=3[N:18]=[CH:17]2)[S:13][C:12]=1[C:25]([NH2:29])=[O:27])[CH3:9]

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of 49 mg of the above-synthesized methyl 3-[1-(2-chlorophenyl)ethoxy]-5-(3H-imidazo[4,5-c]pyridin-3-yl)thiophene-2-carboxylate and 5 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 cool down to room temperature, then another 5 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 to yield the title compound.

Workup

temperatureto cool down to room temperature
customThe solvent was removed under vacuum
customthe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-2f065faa948c4800af6b52b8f78d75cb
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273890B2

Reaction notes

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