Cyclohexane ethylacetate → Acetamide, N-[4-[2-(4,5-dihydro-2-methyl-5-oxo-4-phenyl-4-propyl-1H-imidazol-1-yl)acetyl]-3-fluorophenyl]-

HRID 507408Notes

Reaction equation

Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][C:6]=1[F:15])=[O:4].[CH3:16][C:17]1[NH:21][C:20](=[O:22])[C:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([CH2:23][CH2:24][CH3:25])[N:18]=1.C(=O)([O-])[O-].[K+].CC(C)=O.[K+].C1CCCCC1.C(OCC)(=O)C>C(OCC)(=O)C>[F:15][C:6]1[CH:7]=[C:8]([NH:11][C:12](=[O:14])[CH3:13])[CH:9]=[CH:10][C:5]=1[C:3](=[O:4])[CH2:2][N:21]1[C:20](=[O:22])[C:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([CH2:23][CH2:24][CH3:25])[N:18]=[C:17]1[CH3:16]

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of N-[4-(2-bromo-acetyl)-3-fluoro-phenyl]-acetamide (1.1 g, 2.8 mmol) and (+/−)-2-methyl-5-phenyl-5-propyl-3,5-dihydro-imidazol-4-one (541 mg, 2.5 mmol) in 5 mL acetone potassium carbonate (698 mg, 5 mmol) is added and the reaction mixture is heated at 70° C. for 10 min in the microwave oven (Biotage Initiator). The mixture is cooled to room temperature, filtered and the filtrate evaporated to yield the crude product which is subjected to flash chromatography. ISCO Companion CombiFlash, 40 g silica gel, cyclohexane/ethyl acetate-gradient, ethyl acetate 0-100% to give (+/−)-N-{3-fluoro-4-[2-(2-methyl-5-oxo-4-phenyl-4-propyl-4,5-dihydro-imidazol-1-yl)-acetyl]-phenyl}-acetamide (956 mg, 71%). LC/MS at 254 nm; [M+H] 410; Rt 2.850 min

Workup

additionis added
temperatureThe mixture is cooled to room temperature
filtrationfiltered
customthe filtrate evaporated
customto yield the crude product which

Sources & evidence

ORD record: ord-f8417bb097cb46c390a001e21369ec6b
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786155B2

Reaction notes

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