4-[4-(trifluoromethoxy)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one → 2-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-4-(4-trifluoromethoxyphenyl)-3(2H,4H)-1,2,4-triazolone

HRID 129124

Reaction equation

HRID 129124 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([C@@H:12](O)[CH3:13])[CH2:11][O:10]1.[F:15][C:16]([F:31])([F:30])[O:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH:28]=[N:27][NH:26][C:25]2=[O:29])=[CH:20][CH:19]=1>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([O:10][CH2:11]1)[C@H:12]([N:26]1[C:25](=[O:29])[N:24]([C:21]2[CH:20]=[CH:19][C:18]([O:17][C:16]([F:15])([F:31])[F:30])=[CH:23][CH:22]=2)[CH:28]=[N:27]1)[CH3:13]

Participants

3

Reactant 2

HCID 14809314-[4-(trifluoromethoxy)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-oneHCID 10631861(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanol

Product 1

HCID 105985682-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-4-(4-trifluoromethoxyphenyl)-3(2H,4H)-1,2,4-triazoloneYield 62.5%

Procedure

In the same manner as in Reference Example 5, starting from 1.36 g of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol and 1.33 g of 4-(4-trifluoromethoxyphenyl)-3(2H,4H)-1,2,4-triazolone, 2-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-4-(4-trifluoromethoxyphenyl)-3(2H,4H)-1,2,4-triazolone (1.45 g) was obtained as colorless prisms.

Sources & evidence

ORD record
ord-e1dd7998e4aa4318a9d3ba5046e08f8d
Source dataset
uspto-grants-1995_11
Patent number
US05466820

Linked notes

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