Ethyl Acetate → HCID 67308959, compound

HRID 1615603Notes

Reaction equation

[C:1]([O:5][C:6]([C:8]1[N:9]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[C:10]2[C:15]([C:16]=1[N:17]=[C:18]=[O:19])=[CH:14][C:13]([C:20]([F:23])([F:22])[F:21])=[CH:12][CH:11]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:34][O:35][C:36]([C:38]1[C:42]([NH2:43])=[CH:41][S:40][CH:39]=1)=[O:37].C(OCC)(=O)C>FC(C1C=CC=CC=1)(F)F>[C:1]([O:5][C:6]([C:8]1[N:9]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[C:10]2[C:15]([C:16]=1[NH:17][C:18]([NH:43][C:42]1[C:38]([C:36]([O:35][CH3:34])=[O:37])=[CH:39][S:40][CH:41]=1)=[O:19])=[CH:14][C:13]([C:20]([F:23])([F:22])[F:21])=[CH:12][CH:11]=2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 1-benzyloxycarbonyl-3-isocyanato-5-trifluoromethylindole-2-carboxylic acid tert-butyl ester 5E (˜4.10 mmol) in trifluoromethylbenzene (10 mL) was added 4-aminothiophene-3-carboxylic acid methyl ester 5F (1.30 g, 8.28 mmol). The reaction mixture was heated in a microwave reactor at 150° C. for 30 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 1-benzyloxycarbonyl-3-[3-(4-methoxycarbonylthiophen-3-yl)-ureido]-5-trifluoromethyl-1H-indole-2-carboxylic acid tert-butyl ester 5G (1.89 g, 3.06 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-84ea3e4103024845ac82a6a921d0cbc5
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765757B2

Reaction notes

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