HCID 44554255, compound → HCID 44554254, compound

HRID 1254046Notes

Reaction equation

HRID 1254046 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:31])[CH:28]([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:31])[CH:28]([F:29])[F:30])=[CH:23][CH:22]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 44554255HCID 44554255, compound

Product 1

HCID 44554254HCID 44554254, 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-difluoroethanone (Example 56) following the procedure described for Example 55. 1H NMR (500 MHz, (CDCl3): 8.65 (d, 1H), 8.38 (d, 1H), 8.04 (d, 2H), 7.84 (t, 1H), 7.39 (d, 2H), 7.36 (t, 1H), 7.26 (d, 2H), 7.03 (d, 2H), 5.74 (dt, 1H), 4.58 (m, 1H), 4.12 (s, 3H). LCMS: m/z 458 (M+H)+. The racemic alcohol was resolved on a Chiral AD-H column (20% EtOH/80% hexanes, flow rate 1 mL/min) to give two enantiomers: faster enantiomer's retention time=17.8 min; slower enantiomer's retention time=20.4 min.

Workup

  1. customto give two enantiomers

Sources & evidence

ORD record
ord-6a534afd09c64701b8d45f784e0655d7
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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