Ammonia → 5-(5-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)-3-{[2-(trifluoromethyl)benzyl]oxy}thiophene-2-carboxamide

HRID 2391590Notes

Reaction equation

[CH3:1][O:2][C:3]1[N:8]=[C:7]2[N:9]([C:12]3[S:16][C:15]([C:17]([O:19]C)=O)=[C:14]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:29]([F:32])([F:31])[F:30])[CH:13]=3)[CH:10]=[N:11][C:6]2=[CH:5][CH:4]=1.[NH3:33]>CO>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[N:9]([C:12]3[S:16][C:15]([C:17]([NH2:33])=[O:19])=[C:14]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:29]([F:32])([F:31])[F:30])[CH:13]=3)[CH:10]=[N:11][C:6]2=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 0.74 g of methyl 5-(5-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)-3-{[2-(trifluoromethyl)benzyl]oxy}thiophene-2-carboxylate (compound B7b) and 200 ml of a saturated solution of ammonia in methanol was stirred in an autoclave at 130° C. for 10 h. The reaction mixture was allowed to cool down to room temperature and concentrated to about half of the volume. The precipitated solid was filtered, dissolved in 4 ml methanol/DMSO (1:1) and purified by preparative HPLC (water/acetonitrile, elution gradient 9/1 to 1/9 (v/v)). After lyophilization the obtained solid was crystallized with dichloromethane/n-hexane to give the title compound.

Workup

temperatureto cool down to room temperature
concentrationconcentrated to about half of the volume
filtrationThe precipitated solid was filtered
dissolutiondissolved in 4 ml methanol/DMSO (1:1)
custompurified by preparative HPLC (water/acetonitrile, elution gradient 9/1 to 1/9 (v/v))
customAfter lyophilization the obtained solid was crystallized with dichloromethane/n-hexane

Sources & evidence

ORD record: ord-a43706a3e0834483bb658d2c1e0fb29d
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273890B2

Reaction notes

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