1-Bromo-3-ethynylbenzene → (5R)-2-amino-5-(3-bromophenyl)-5-[4-(difluoromethoxy)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one

HRID 30547Notes

Reaction equation

HRID 30547 reaction equation
BrC1C=CC=C(C#C)C=1.[NH2:10][C:11]1[N:15]([CH3:16])[C:14](=[O:17])[C:13]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Br:34])[CH:29]=2)([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH:25]([F:27])[F:26])=[CH:20][CH:19]=2)[N:12]=1>CO>[NH2:10][C:11]1[N:15]([CH3:16])[C:14](=[O:17])[C@:13]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Br:34])[CH:29]=2)([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH:25]([F:27])[F:26])=[CH:20][CH:19]=2)[N:12]=1

Participants

4

Reactant 2

HCID 114808181-Bromo-3-ethynylbenzeneHCID 597903072-amino-4-(3-bromophenyl)-4-(4-(difluoromethoxy)phenyl)-1-methyl-1H-imidazol-5(4H)-one

Product 1

HCID 16113755(5R)-2-amino-5-(3-bromophenyl)-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-d, and employing 1-bromo-3-ethynylbenzene in step a, the racemic mixture of 2-amino-5-(3-bromophenyl)-5-[4-(difluoromethoxy)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one was obtained and separated by chiral chromatography technique (Chiralcel OJ, 2×25 cm, using 5% ethanol in 95% 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), 6.72 (brs, 2H), 7.1 (d, J=8.66 Hz, 2H), 7.13-7.35 (m, 2H), 7.38-7.43 (m, 4H), 7.56 (t, J=1.72 Hz, 1H); [a]25=−4 (C=1% in MeOH).

Workup

  1. customwas obtained
  2. customseparated by chiral chromatography technique (Chiralcel OJ, 2×25 cm
  3. customto give the title enantiomer, MS m/e (M+H)+ 332

Sources & evidence

ORD record
ord-12e43d344f1d4913921d73340ca67627
Source dataset
uspto-grants-2008_09
Patent number
US07423158B2

Reaction notes

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