HCID 44554253, compound → HCID 44554252, compound

HRID 1254047Notes

Reaction equation

HRID 1254047 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[N:11][C:10]=2[C:21]2[CH:26]=[CH:25][C:24]([C:27](=[O:32])[C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=2)=[CH:4][CH:3]=1>CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[N:11][C:10]=2[C:21]2[CH:26]=[CH:25][C:24]([CH:27]([OH:32])[C:28]([F:29])([F:30])[F:31])=[CH:23][CH:22]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 44554253HCID 44554253, compound

Product 1

HCID 44554252HCID 44554252, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared from 1-(4-{5-[(4-chlorophenyl)thio]-1-methyl-2-pyridin-2-yl-1H-imidazol-4-yl}phenyl)-2,2,2-trifluoroethanone (Example 58) following the procedure described for Example 55. 1H NMR (500 MHz, (CDCl3): 8.64 (broad s, 1H), 8.39 (broad d, 1H), 7.84 (t, 1H), 7.36 (t, 1H), 7.25 (d, 2H), 7.23 (d, 2H), 7.06 (d, 2H), 7.03 (d, 2H), 4.59 (m, 1H), 4.15 (s, 3H). LCMS: m/z 476 (M+H)+.)+. The racemic alcohol was resolved on a Chiral OJ column (20% EtOH/80% hexanes, flow rate 1 mL/min) to give two enantiomers: faster enantiomer's retention time=15.8 min; slower enantiomer's retention time=18.9 min.

Workup

  1. customto give two enantiomers

Sources & evidence

ORD record
ord-acd421d4b59d456096b6d18929838eea
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

Loading…