HCID 14207262, compound → 6-[1-Hydroxy-1-phenyl-2-(imidazol-1-yl)ethyl]-3,4-dihydrocarbostyril

HRID 414558Notes

Reaction equation

[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:9]1([CH2:14][C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[NH:23][C:22](=[O:27])[CH2:21][CH2:20]3)=[O:16])[CH:13]=[CH:12][N:11]=[CH:10]1>CCOCC.O1CCCC1>[OH:16][C:15]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[NH:23][C:22](=[O:27])[CH2:21][CH2:20]2)([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:14][N:9]1[CH:13]=[CH:12][N:11]=[CH:10]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3 ml of 3M phenylmagnesium bromide in ether was added to a suspension of 1.0 g of 6-(imidazol-1-yl acetyl)-3,4-dihydrocarbostyril in 25 ml of tetrahydrofuran at 0° C., the mixture stirred for 30 minutes at 0° C., then at 25° C. for 18 hours. The reaction was quenched with 10 ml of water and extracted with 10% methanol in methylene chloride. The organic extract was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield a gum which was chromatographed on silica gel, eluting with 5% methanol in methylene chloride, to give 6-[1-hydroxy-1-phenyl-2-(imidazol-1-yl)ethyl]-3,4-dihydrocarbostyril as a foam.

Workup

waitat 25° C. for 18 hours
customThe reaction was quenched with 10 ml of water
extractionextracted with 10% methanol in methylene chloride
extractionThe organic extract
washwas washed with water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customto yield a gum which
customwas chromatographed on silica gel
washeluting with 5% methanol in methylene chloride

Sources & evidence

ORD record: ord-6f039caaa7b5468e83fa8f67825900b0
Source dataset: uspto-grants-1988_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04792561

Reaction notes

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