(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanol → 2-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-4-[4-(4-benzyl-1-piperazinyl)phenyl]-3(2H,4H)-1,2,4-triazolone

HRID 1491750Notes

Reaction equation

HRID 1491750 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.[CH2:15]([N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:33]=[CH:32][C:31]([N:34]3[CH:38]=[N:37][NH:36][C:35]3=[O:39])=[CH:30][CH:29]=2)[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=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:36]1[C:35](=[O:39])[N:34]([C:31]2[CH:30]=[CH:29][C:28]([N:25]3[CH2:24][CH2:23][N:22]([CH2:15][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH2:27][CH2:26]3)=[CH:33][CH:32]=2)[CH:38]=[N:37]1)[CH3:13]

Participants

3

Reactant 2

HCID 10631861(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanolHCID 193736904-[4-(4-benzyl-1-piperazinyl)phenyl]-3(2H,4H)-1,2,4-triazolone

Product 1

HCID 152857532-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-4-[4-(4-benzyl-1-piperazinyl)phenyl]-3(2H,4H)-1,2,4-triazoloneYield 19%

Procedure

In the same manner as in Reference Example 5, starting from 681 mg of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol and 1.0 g of 4-[4-(4-benzyl-1-piperazinyl)phenyl]-3(2H,4H)-1,2,4-triazolone, 2-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-4-[4-(4-benzyl-1-piperazinyl)phenyl]-3(2H,4H)-1,2,4-triazolone (293 mg) was obtained as a colorless powder.

Sources & evidence

ORD record
ord-02626517855745dfb85eb85ea635ecde
Source dataset
uspto-grants-1994_12
Patent number
US05371101

Reaction notes

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