HCID 66917344, compound → HCID 66917205, compound

HRID 2167482Notes

Reaction equation

C([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([F:32])=[C:17]2[C:22]=1[NH:21][CH:20]=[C:19]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)[C:18]2=[O:31])C1C=CC=CC=1>[C].[Pd].C(O)C>[F:32][C:16]1[CH:15]=[CH:14][C:13]([O:12][CH2:11][CH2:10][CH2:9][OH:8])=[C:22]2[C:17]=1[C:18](=[O:31])[C:19]([C:23]1[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=1)=[CH:20][NH:21]2

Participants

Conditions

Temperature: 50 °C

Procedure

8-(3-Benzyloxypropoxy)-5-fluoro-3-(4-methoxyphenyl)-1H-quinolin-4-one (1.95 g, 4.49 mmol) and a 10% palladium carbon (720 mg) were added to ethanol (50 ml). The mixture was stirred at 50° C. for 7.5 hours under a hydrogen atmosphere (1 atmosphere) and subjected to a catalytic reduction. The reaction mixture was cooled to room temperature, and filtration with Celite was conducted to remove the solvent. The filtrate was concentrated under reduced pressure. The residue was then purified by silica gel column chromatography (dichloromethane:methanol=80:1→20:1). The purified product was concentrated under reduced pressure, and the residue was concentrated to dryness to thereby obtain 820 mg of pale dark brown amorphous solid 5-fluoro-8-(3-hydroxypropoxy)-3-(4-methoxyphenyl)-1H-quinolin-4-one (yield: 53%).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltration with Celite
customto remove the solvent
concentrationThe filtrate was concentrated under reduced pressure
customThe residue was then purified by silica gel column chromatography (dichloromethane:methanol=80:1→20:1)
concentrationThe purified product was concentrated under reduced pressure
concentrationthe residue was concentrated to dryness

Sources & evidence

ORD record: ord-12643b48d0d54f018dd697f0214f864b
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045464B2

Reaction notes

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