2,4-Dihydro-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-3H-1,2,4-triazol-3-one → 2-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-3(2H,4H)-1,2,4-triazolone

HRID 129131Notes

Reaction equation

HRID 129131 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.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][N:26]([C:29]3[CH:34]=[CH:33][C:32]([N:35]4[CH:39]=[N:38][NH:37][C:36]4=[O:40])=[CH:31][CH:30]=3)[CH2:25][CH2:24]2)=[CH:19][CH:18]=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:37]1[C:36](=[O:40])[N:35]([C:32]2[CH:33]=[CH:34][C:29]([N:26]3[CH2:27][CH2:28][N:23]([C:20]4[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=4)[CH2:24][CH2:25]3)=[CH:30][CH:31]=2)[CH:39]=[N:38]1)[CH3:13]

Participants

3

Reactant 2

HCID 42465972,4-Dihydro-4-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-3H-1,2,4-triazol-3-oneHCID 10631861(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanol

Product 1

HCID 152857572-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-3(2H,4H)-1,2,4-triazoloneYield 30.4%

Procedure

In the same manner as in Reference Example 5, starting from 543 mg of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol and 809 mg of 4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-3(2H,4H)-1,2,4-triazolone prepared by a method described in Journal of Medicinal Chemistry, vol. 27, page 894 (1984), 2-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-3(2H,4H)-1,2,4-triazolone (373 mg) was obtained as colorless prisms.

Workup

  1. customprepared by a method

Sources & evidence

ORD record
ord-fe36d733013f404db050d9fc8e8dcc42
Source dataset
uspto-grants-1995_11
Patent number
US05466820

Reaction notes

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