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

HRID 129128Notes

Reaction equation

HRID 129128 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.[CH:15]([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)([CH3:17])[CH3:16].FC1C=C(F)C=CC=1[C@]1([C@H](O)C)CO1>>[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:22]=[CH:23][C:18]([CH:15]([CH3:17])[CH3:16])=[CH:19][CH:20]=2)[CH:28]=[N:27]1)[CH3:13]

Participants

4

Reactant 3

HCID 14801364-(4-isopropylphenyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneHCID 10536015(1R)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanolHCID 10631861(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanol

Product 1

HCID 186576342-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-4-(4-isopropylphenyl)-3(2H,4H)-1,2,4-triazoloneYield 27.9%

Procedure

In the same manner as in Reference Example 5, starting from 1.72 g of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol and 1.68 g of 4-(4-isopropylphenyl)-3(2H,4H)-1,2,4-triazolone, an about 1:1 mixture (0.89 g) of 2-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]- 4-(4-isopropylphenyl)-3 (2H, 4H)-1,2,4-triazolone and (1R)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol was obtained.

Sources & evidence

ORD record
ord-b6d209bfdbde4de998469851d57cc154
Source dataset
uspto-grants-1995_11
Patent number
US05466820

Reaction notes

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