Ethyl Acetate → HCID 86654950, compound

HRID 1615599Notes

Reaction equation

[C:1]([O:5][C:6]([C:8]1[N:9]([C:35]2[CH:39]=[CH:38][S:37][CH:36]=2)[C:10]2[C:15]([C:16]=1[NH:17][C:18]([NH:20][C:21]1[C:25]([C:26]([O:28]C)=O)=[CH:24][S:23][CH:22]=1)=[O:19])=[C:14]([CH3:30])[C:13]([C:31]([F:34])([F:33])[F:32])=[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[N:9]([C:35]2[CH:39]=[CH:38][S:37][CH:36]=2)[C:10]2[C:15]([C:16]=1[N:17]1[C:26](=[O:28])[C:25]3=[CH:24][S:23][CH:22]=[C:21]3[NH:20][C:18]1=[O:19])=[C:14]([CH3:30])[C:13]([C:31]([F:34])([F:32])[F:33])=[CH:12][CH:11]=2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-[3-(4-methoxycarbonyl-thiophen-3-yl)-ureido]-1-thiophen-3-yl-methyl-5-trifluoromethyl-1H-indole-2-carboxylic acid tert-butyl ester 1H (1.50 g, 2.59 mmol) in anhydrous methanol (10 mL) was added a 0.5 M solution of sodium methoxide (7.8 mL, 3.90 mmol). The reaction mixture was heated in a microwave reactor at 100° C. for 20 minutes. Ethyl acetate (100 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 to provide 3-(2,4-dioxo-1,2-dihydro-4H-thieno[3,4-d]pyrimidin-3-yl)-1-thiophen-3-yl-methyl-5-trifluoromethyl-1H-indole-2-carboxylic acid tert-butyl ester 1J which was used in the next step without further purification.

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

Sources & evidence

ORD record: ord-7af0cfb2f8cb43858756cdd9b6357549
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765757B2

Reaction notes

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