Hydrochloric Acid → HCID 19434859, compound

HRID 1736223Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:18]([F:19])=[CH:17][C:16]([F:20])=[C:15]([NH:21][CH2:22][CH2:23][CH2:24][C:25]([O:27]CC)=[O:26])[C:11]=3[C:12](=[O:14])[CH:13]=2)=[CH:4][C:3]=1[F:30].[OH-].[Na+].Cl>C(O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:18]([F:19])=[CH:17][C:16]([F:20])=[C:15]([NH:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])[C:11]=3[C:12](=[O:14])[CH:13]=2)=[CH:4][C:3]=1[F:30]

Participants

Conditions

Temperature: 50 °C

Procedure

303 mg (0.722mmol) of the above 2-(4-amino-3-fluorophenyl)-5-(3-ethoxycarbonylpropylamino)-6,8-difluoro-4H-1-benzopyran-4-one was dissolved in 20 mL of ethanol, 1.5 mL of a 2N aqueous solution of sodium hydroxide was added and the mixture was stirred at 50° C. for 5 hours. The reaction solution was cooled on ice and adjusted to pH 7 by addition of hydrochloric acid thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol:acetic acid=20:1:0.1) to give 115 mg of Compound 141 (yield: 41%).

Workup

temperatureThe reaction solution was cooled on ice
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with an aqueous saturated solution of sodium chloride
dry with materialdried over anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe residue was purified by silica gel column chromatography (chloroform:methanol:acetic acid=20:1:0.1)

Sources & evidence

ORD record: ord-5a671929881146b5b0781b92035263d5
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05539112

Reaction notes

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