Ammonia → 5-(3H-Imidazo[4,5-c]pyridin-3-yl)-3-{[2-(trifluoromethyl)benzyl]oxy}thio-phene-2-carboxamide

HRID 2391570Notes

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][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:30])([F:29])[F:28])[CH:11]=2)[CH:2]=1.[NH3:31]>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]([NH2:31])=[O:17])=[C:12]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:28])([F:29])[F:30])[CH:11]=2)[CH:2]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 1.40 g of methyl 5-(3H-imidazo[4,5-c]pyridin-3-yl)-3-{[2-(trifluoromethyl)benzyl]oxy}thiophene-2-carboxylate (compound B1b) and 65 ml of a saturated solution of ammonia in methanol were stirred in an autoclave at 130° C. for 7 h. The mixture was allowed to cool down to room temperature and concentrated to about half of the volume. The precipitated solid was filtered, widely dissolved in 500 ml of methanol upon heating and filtered again. The filtrate was concentrated to about 25 ml upon which solid precipitated. It was filtered, dissolved in acetonitrile containing small amounts of water and finally the solution was lyophilized to give the title compound as a colorless powder.

Workup

temperatureto cool down to room temperature
concentrationconcentrated to about half of the volume
filtrationThe precipitated solid was filtered
dissolutionwidely dissolved in 500 ml of methanol
temperatureupon heating
filtrationfiltered again
concentrationThe filtrate was concentrated to about 25 ml upon which solid
customprecipitated
filtrationIt was filtered
dissolutiondissolved in acetonitrile containing small amounts of water

Sources & evidence

ORD record: ord-8afd6380954747f68be5238444b60133
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273890B2

Reaction notes

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