Ethyl Acetate → HCID 86654953, compound

HRID 1615604Notes

Reaction equation

[C:1]([O:5][C:6]([C:8]1[N:9](C(OCC2C=CC=CC=2)=O)[C:10]2[C:15]([C:16]=1[NH:17][C:18]([NH:20][C:21]1[C:25]([C:26](OC)=[O:27])=[CH:24][S:23][CH:22]=1)=[O:19])=[CH:14][C:13]([C:30]([F:33])([F:32])[F:31])=[CH:12][CH:11]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+].C(OCC)(=O)C>CO>[C:1]([O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([C:16]=1[N:17]1[C:26](=[O:27])[C:25]3=[CH:24][S:23][CH:22]=[C:21]3[NH:20][C:18]1=[O:19])=[CH:14][C:13]([C:30]([F:33])([F:31])[F:32])=[CH:12][CH:11]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 1-benzyloxycarbonyl-3-[3-(4-methoxycarbonylthiophen-3-yl)-ureido]-5-trifluoromethyl-1H-indole-2-carboxylic acid tert-butyl ester 5G (5.29 g, 8.57 mmol) in anhydrous methanol (50 mL) was added a 0.5 M solution of sodium methoxide (25 mL, 12.5 mmol). The reaction mixture was heated in a microwave reactor at 100° C. for 10 minutes. Ethyl acetate (500 mL) was added and the organic layer was washed with 1 N hydrochloric acid and brine. The organic layer was dried over sodium sulfate. The organic solvent was evaporated under reduced pressure. The crude product was purified by flash column chromatography to provide 3-(2,4-dioxo-1,2-dihydro-4H-thieno[3,4-d]pyrimidin-3-yl)-5-trifluoromethyl-1H-indole-2-carboxylic acid tert-butyl ester 5H (3.36 g, 7.45 mmol).

Workup

washthe organic layer was washed with 1 N hydrochloric acid and brine
dry with materialThe organic layer was dried over sodium sulfate
customThe organic solvent was evaporated under reduced pressure
customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record: ord-8afdcb53a4124413b5ad5bf4a4327721
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765757B2

Reaction notes

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