Potassium Carbonate → 4-{[7-(Cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]oxy}benzonitrile

HRID 469219Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].F[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.[CH:16]1([NH:22][C:23]2[CH:32]=[C:31]3[C:26]([C:27](=[O:39])[C:28]([OH:38])=[CH:29][N:30]3[CH:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:25][C:24]=2[F:40])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[Cl-].[NH4+]>CN(C=O)C>[CH:16]1([NH:22][C:23]2[CH:32]=[C:31]3[C:26]([C:27](=[O:39])[C:28]([O:38][C:8]4[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=4)=[CH:29][N:30]3[CH:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:25][C:24]=2[F:40])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

Conditions

Temperature: 80 °C

Procedure

690 mg of potassium carbonate and 363 mg of 4-fluorobenzonitrile were added to a 10 ml DMF solution of 344 mg of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-3-hydroxyquinolin-4(1H)-one, followed by overnight stirring at 80° C. After completion of the reaction and subsequent cooling to room temperature, aqueous saturated ammonium chloride was added to the reaction mixture, followed by extraction with ethyl acetate. After drying over anhydrous sodium sulfate and subsequent evaporation under a reduced pressure, the residue was purified by silica gel column chromatography to obtain 100 mg of 4-{[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]oxy}benzonitrile.

Workup

customAfter completion of the reaction
temperaturesubsequent cooling to room temperature
extractionfollowed by extraction with ethyl acetate
dry with materialAfter drying over anhydrous sodium sulfate and subsequent evaporation under a reduced pressure
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-f8b0f19cf6004b2daf17c82ad6db5c10
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629126B2

Reaction notes

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