Methanol → HCID 22603285, compound

HRID 1799300Notes

Reaction equation

[CH2:1](N(C(C)C)C(C)C)C.C[C:11]1[O:12][C:13](=[O:28])[C:14](=[CH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=2)[N:15]=1.[CH3:29][OH:30]>[C].[Pd]>[C:29]([NH:15][CH:14]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:25])([F:26])[F:27])=[CH:19][CH:18]=1)[C:13]([O:12][CH3:11])=[O:28])(=[O:30])[CH3:1]

Participants

Conditions

Temperature: 60 °C

Procedure

N-Ethyl-N,N-diisopropylamine (2.50 g, 19.4 mmol) was added to a methanol (50 mL) solution of 2-methyl-4-[4-(trifluoromethoxy)benzylidene]-1,3-oxazol-5(4H)-one (5.00 g, 18.4 mmol) prepared in Reference Example 3 (3d), at room temperature. The mixture was stirred at 60° C. for 4 hours. The reaction solution was cooled to room temperature, and then 10% palladium-carbon (wet, 2.2 g) was added thereto. The resulting mixture was stirred under a hydrogen atmosphere (rubber balloon) at room temperature for 2 hours. The reaction solution was filtered, and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate, 1:1 and 4:5, V/V) to give 4.56 g of the title compound (light yellow crystal, yield: 81%).

Workup

temperatureThe reaction solution was cooled to room temperature
stirringThe resulting mixture was stirred under a hydrogen atmosphere (rubber balloon) at room temperature for 2 hours
filtrationThe reaction solution was filtered
customthe solvent was evaporated
customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate, 1:1 and 4:5, V/V)

Sources & evidence

ORD record: ord-efcbe7d9375a48a9a8d034faa07cd7fc
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08344029B2

Reaction notes

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