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

HRID 2391604Notes

Reaction equation

[F:1][CH:2]([F:30])[O:3][C:4]1[CH:29]=[CH:28][CH:27]=[CH:26][C:5]=1[CH2:6][O:7][C:8]1[CH:12]=[C:11]([N:13]2[C:17]3[CH:18]=[N:19][CH:20]=[CH:21][C:16]=3[N:15]=[CH:14]2)[S:10][C:9]=1[C:22]([O:24]C)=O.[NH3:31]>CO>[F:30][CH:2]([F:1])[O:3][C:4]1[CH:29]=[CH:28][CH:27]=[CH:26][C:5]=1[CH2:6][O:7][C:8]1[CH:12]=[C:11]([N:13]2[C:17]3[CH:18]=[N:19][CH:20]=[CH:21][C:16]=3[N:15]=[CH:14]2)[S:10][C:9]=1[C:22]([NH2:31])=[O:24]

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of 37.5 mg of methyl 3-{[2-(difluoromethoxy)benzyl]oxy}-5-(3H-imidazo[4,5-c]pyridin-3-yl)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 a mixture of acetonitrile and methanol (9:1 (v/v)) and purified by preparative HPLC (water/acetonitrile, elution gradient 9/1 to 1/9 (v/v)) to obtain the title compound.

Workup

concentrationThe reaction mixture is concentrated to dryness
dissolutionthe resulting residue is dissolved in a mixture of acetonitrile and methanol (9:1 (v/v))
custompurified by preparative HPLC (water/acetonitrile, elution gradient 9/1 to 1/9 (v/v))

Sources & evidence

ORD record: ord-aa72a401c5024ce384ff330a7deb339f
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273890B2

Reaction notes

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