HCID 90229603, compound → HCID 90229275, compound

HRID 1505764Notes

Reaction equation

[F:1][C:2]([F:27])([F:26])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([NH:11][C:12]1[CH:13]=[C:14]([C:21]([O:23]CC)=[O:22])[C:15]2[O:19][CH2:18][CH2:17][C:16]=2[CH:20]=1)=[O:10]>CCO.[OH-].[Na+]>[F:26][C:2]([F:1])([F:27])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([NH:11][C:12]1[CH:13]=[C:14]([C:21]([OH:23])=[O:22])[C:15]2[O:19][CH2:18][CH2:17][C:16]=2[CH:20]=1)=[O:10]

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of ethyl 5-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-2,3-dihydro-1-benzofuran-7-carboxylate (220 mg) obtained in Step 2 in EtOH (5 mL), 1N aqueous sodium hydroxide solution (1 mL) was added and the mixture was stirred at 80° C. for 4 hours. The reaction mixture was cooled to room temperature, and EtOH was removed under reduced pressure. To the residue was added water, and the solution was acidified to pH 3 with 1N hydrochloric acid under ice-cooling and extracted with ethyl acetate. The organic layer was washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the titled compound (195 mg) as slightly yellow powder.

Workup

additionwas added
temperatureThe reaction mixture was cooled to room temperature
customEtOH was removed under reduced pressure
additionTo the residue was added water
temperaturecooling
extractionextracted with ethyl acetate
washThe organic layer was washed sequentially with water and brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-4b65986685884212a4348b4cbe52e09e
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216968B2

Reaction notes

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