3-(Trifluoromethyl)benzoyl chloride → 6-[4-(2,5-Bis-trifluoromethyl-benzoyl)-piperazin-1-yl]-2,4-dimethyl-2H-[1,2,4]triazine-3,5-dione

HRID 1917114Notes

Reaction equation

HRID 1917114 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[CH3:14][N:15]1[C:20](=[O:21])[N:19]([CH3:22])[C:18](=[O:23])[C:17]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[N:16]1>>[CH3:14][N:15]1[C:20](=[O:21])[N:19]([CH3:22])[C:18](=[O:23])[C:17]([N:24]2[CH2:25][CH2:26][N:27]([C:6](=[O:7])[C:5]3[CH:9]=[CH:10][CH:11]=[C:3]([C:2]([F:13])([F:12])[F:1])[CH:4]=3)[CH2:28][CH2:29]2)=[N:16]1.[F:1][C:2]([F:13])([F:12])[C:9]1[CH:10]=[CH:11][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][C:5]=1[C:6]([N:27]1[CH2:26][CH2:25][N:24]([C:17]2[C:18](=[O:23])[N:19]([CH3:22])[C:20](=[O:21])[N:15]([CH3:14])[N:16]=2)[CH2:29][CH2:28]1)=[O:7]

Participants

4

Reactant 2

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 337810652,4-dimethyl-6-(piperazin-1-yl)-1,2,4-triazine-3,5(2H,4H)-dione

Product 2

HCID 582697682,4-dimethyl-6-[4-(3-trifluoromethyl-benzoyl)-piperazin-1-yl]-2H-[1,2,4]triazine-3,5-dioneHCID 582698156-[4-(2,5-Bis-trifluoromethyl-benzoyl)-piperazin-1-yl]-2,4-dimethyl-2H-[1,2,4]triazine-3,5-dioneYield 75%

Procedure

The compound 44 (solid) is prepared from 3-trifluoromethyl-benzoyl chloride and from the intermediate 12a according to the synthesis method 2 under the operating conditions described for Example 40 (yield: 75%).

Workup

  1. customaccording to the synthesis method 2 under the operating conditions

Sources & evidence

ORD record
ord-6100cc984e2343cebc5f70cbb0fc3e7c
Source dataset
uspto-grants-2013_12
Patent number
US08618287B2

Reaction notes

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