Hydrochloric Acid → (+/-)-3-[2-(4-Amino-2-fluoro-phenyl)-2-oxo-ethyl]-2-methyl-5-phenyl-5-propyl-3,5-dihydro-imidazol-4-one

HRID 507409Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([NH:27]C(=O)C)[CH:5]=[CH:6][C:7]=1[C:8](=[O:26])[CH2:9][N:10]1[C:14](=[O:15])[C:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([CH2:16][CH2:17][CH3:18])[N:12]=[C:11]1[CH3:25].Cl>C(O)C>[NH2:27][C:4]1[CH:5]=[CH:6][C:7]([C:8](=[O:26])[CH2:9][N:10]2[C:14](=[O:15])[C:13]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([CH2:16][CH2:17][CH3:18])[N:12]=[C:11]2[CH3:25])=[C:2]([F:1])[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

(+/−)-N-{3-fluoro-4-[2-(2-methyl-5-oxo-4-phenyl-4-propyl-4,5-dihydro-imidazol-1-yl)-acetyl]-phenyl}-acetamide (956 mg, 1.8 mmol) is dissolved in 10 mL ethanol and concentrated hydrochloric acid (192 uL, 1.9 mmol) is added. The mixture is heated to 100° C. in the microwave oven (Biotage Initiator) for 30 min. Subsequently the solvent is evaporated and the residue is suspended in concentrated sodium hydrogen carbonate solution and dichloromethane. This mixture is extracted three times with dichloromethane. The organic phase is dried with sodium sulfate, filtrated and evaporated to yield (+/−)-3-[2-(4-amino-2-fluoro-phenyl)-2-oxo-ethyl]-2-methyl-5-phenyl-5-propyl-3,5-dihydro-imidazol-4-one (325 mg, 40%) as light brown foam. LC/MS at 254 nm; [M+H] 368; Rt 2.616 min.

Workup

customSubsequently the solvent is evaporated
extractionThis mixture is extracted three times with dichloromethane
dry with materialThe organic phase is dried with sodium sulfate
filtrationfiltrated
customevaporated

Sources & evidence

ORD record: ord-94cc97d8689e48beae93d0b9ebbf63f8
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786155B2

Reaction notes

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