Ammonia → HCID 68766308, compound

HRID 2391665Notes

Reaction equation

[Si:1]([O:8][CH2:9][C:10]1[N:15]=[CH:14][C:13]2[N:16]=[CH:17][N:18]([C:19]3[S:23][C:22]([C:24]([O:26]C)=O)=[C:21]([O:28][CH:29]([C:31]4[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=4[C:38]([F:41])([F:40])[F:39])[CH3:30])[CH:20]=3)[C:12]=2[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH3:42]>CO>[Si:1]([O:8][CH2:9][C:10]1[N:15]=[CH:14][C:13]2[N:16]=[CH:17][N:18]([C:19]3[S:23][C:22]([C:24]([NH2:42])=[O:26])=[C:21]([O:28][CH:29]([C:31]4[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=4[C:38]([F:40])([F:39])[F:41])[CH3:30])[CH:20]=3)[C:12]=2[CH:11]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 127.5 °C

Procedure

A mixture of 2.22 g of methyl 5-[6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1H-imidazo[4,5-c]pyridin-1-yl]-3-{-1-[4-fluoro-2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxylate and 168 ml of a saturated solution of ammonia in methanol is stirred in a microwave vial at 125-130° C. for 4 h in the microwave cavity. The reaction mixture is concentrated to dryness and the resulting residue is purified by flash chromatography [Silica gel, eluent: ethyl acetate/cyclohexane, elution gradient of 0/100 (v/v) to 70/30 (v/v)] to yield the title product.

Workup

concentrationThe reaction mixture is concentrated to dryness
customthe resulting residue is purified by flash chromatography [Silica gel, eluent: ethyl acetate/cyclohexane, elution gradient of 0/100 (v/v) to 70/30 (v/v)]

Sources & evidence

ORD record: ord-a30be812f61a421b93a7998677f44880
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273890B2

Reaction notes

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