HCID 57435852, compound → (5R)-2-Amino-5-(3-bromo-4-fluorophenyl)-5-[4-(difluoromethoxy)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one

HRID 30548Notes

Reaction equation

HRID 30548 reaction equation
BrC1C=C(C#C)C=CC=1F.[NH2:11][C:12]1[N:16]([CH3:17])[C:15](=[O:18])[C:14]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[C:31]([Br:36])[CH:30]=2)([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH:26]([F:28])[F:27])=[CH:21][CH:20]=2)[N:13]=1>CO>[NH2:11][C:12]1[N:16]([CH3:17])[C:15](=[O:18])[C@:14]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[C:31]([Br:36])[CH:30]=2)([C:19]2[CH:20]=[CH:21][C:22]([O:25][CH:26]([F:28])[F:27])=[CH:23][CH:24]=2)[N:13]=1

Participants

4

Reactant 2

HCID 57435852HCID 57435852, compoundHCID 597903432-Amino-5-(3-bromo-4-fluorophenyl)-5-[4-(difluoromethoxy)phenyl]-3,5-dihydro-3-methyl-4H-imidazol-4-one

Product 1

HCID 16113757(5R)-2-Amino-5-(3-bromo-4-fluorophenyl)-5-[4-(difluoromethoxy)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using essentially the same procedure described in Example 1, steps a-c, and employing 3-bromo-4-fluoro-1-ethynylbenzene the racemic mixture of 2-amino-5-(3-bromo-4-fluorophenyl)-5-[4-(difluoromethoxy)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one was obtained and separated by chiral chromatography technique (Chiralcel OJ, 0.46×10 cm, using 15% ethanol in 85% hexane and diethylamine as the mobile phase) to give the title enantiomer, MS m/e (M+H)+ 332; 1H NMR (400 MHz, DMSO-d6) 2.94 (s, 3H), 6.74 (brs, 2H), 7.1 (d, J=8.75 Hz, 2H), 7.13-7.65 (m, 5H), 7.67 (d, J=2.2 Hz, 1H); [a]25=−22 (C=1% in MeOH).

Workup

  1. customwas obtained
  2. customseparated by chiral chromatography technique (Chiralcel OJ, 0.46×10 cm
  3. customto give the title enantiomer, MS m/e (M+H)+ 332

Sources & evidence

ORD record
ord-f1127cfcd021467a8a36d8532fa3d7c3
Source dataset
uspto-grants-2008_09
Patent number
US07423158B2

Reaction notes

Loading…