5-Fluoro-2-(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 1917113Notes

Reaction equation

HRID 1917113 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:11]([F:14])([F:13])[F:12])=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[CH3:15][N:16]1[C:21](=[O:22])[N:20]([CH3:23])[C:19](=[O:24])[C:18]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[N:17]1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:11]([F:14])([F:13])[F:12])=[C:6]([CH:10]=1)[C:7]([N:28]1[CH2:27][CH2:26][N:25]([C:18]2[C:19](=[O:24])[N:20]([CH3:23])[C:21](=[O:22])[N:16]([CH3:15])[N:17]=2)[CH2:30][CH2:29]1)=[O:8].[F:12][C:11]([F:14])([F:13])[C:5]1[CH:4]=[CH:3][C:2]([C:11]([F:14])([F:13])[F:12])=[CH:10][C:6]=1[C:7]([N:28]1[CH2:27][CH2:26][N:25]([C:18]2[C:19](=[O:24])[N:20]([CH3:23])[C:21](=[O:22])[N:16]([CH3:15])[N:17]=2)[CH2:30][CH2:29]1)=[O:8]

Participants

4

Reactant 2

HCID 27375605-Fluoro-2-(trifluoromethyl)benzoyl chlorideHCID 337810652,4-dimethyl-6-(piperazin-1-yl)-1,2,4-triazine-3,5(2H,4H)-dione

Product 2

HCID 446215306-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2,4-dimethyl-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 86%

Procedure

The compound 42 (solid) is prepared from 5-fluoro-2-trifluoromethyl-benzoyl chloride and from the intermediate 12a according to the synthesis method 2 under the operating conditions described for Example 40 (yield: 86%).

Workup

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

Sources & evidence

ORD record
ord-4da9623dfe8f4733be1a7e8b7621800d
Source dataset
uspto-grants-2013_12
Patent number
US08618287B2

Reaction notes

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