Ethyl Acetate → HCID 86654948, compound

HRID 1615598Notes

Reaction equation

[C:1]([O:5][C:6]([C:8]1[N:9]([C:25]2[CH:29]=[CH:28][S:27][CH:26]=2)[C:10]2[C:15]([C:16]=1[N:17]=[C:18]=[O:19])=[C:14]([CH3:20])[C:13]([C:21]([F:24])([F:23])[F:22])=[CH:12][CH:11]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:30][O:31][C:32]([C:34]1[C:38]([NH2:39])=[CH:37][S:36][CH:35]=1)=[O:33].C(OCC)(=O)C>FC(C1C=CC=CC=1)(F)F>[C:1]([O:5][C:6]([C:8]1[N:9]([C:25]2[CH:29]=[CH:28][S:27][CH:26]=2)[C:10]2[C:15]([C:16]=1[NH:17][C:18]([NH:39][C:38]1[C:34]([C:32]([O:31][CH3:30])=[O:33])=[CH:35][S:36][CH:37]=1)=[O:19])=[C:14]([CH3:20])[C:13]([C:21]([F:23])([F:22])[F:24])=[CH:12][CH:11]=2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 3-isocyanato-1-thiophen-3-yl-methyl-5-trifluoromethyl-1H-indole-2-carboxylic acid tert-butyl ester 1F (˜4.39 mmol) in trifluoromethylbenzene (10 mL) was added 4-aminothiophene-3-carboxylic acid methyl ester 1G (1.38 g, 8.79 mmol). The reaction mixture was heated in a microwave reactor at 150° 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. The crude product was purified by flash column chromatography to provide 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).

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-e2fd286fe9ae4095abc6a28e6c77f04d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765757B2

Reaction notes

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