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 1917115Notes

Reaction equation

HRID 1917115 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](Cl)=[O:6].[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][C:26](=[O:30])[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[CH2:29][CH2:28][N:27]([C:5](=[O:6])[C:4]3[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=3[C:2]([F:13])([F:12])[F:1])[C:26](=[O:30])[CH2:25]2)=[N:16]1.[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:9]([C:2]([F:13])([F:12])[F:1])=[CH:8][C:4]=1[C:5]([N:27]1[CH2:28][CH2:29][N:24]([C:17]2[C:18](=[O:23])[N:19]([CH3:22])[C:20](=[O:21])[N:15]([CH3:14])[N:16]=2)[CH2:25][CH2:26]1)=[O:6]

Participants

4

Reactant 2

HCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 163525032,4-dimethyl-6-(3-oxo-piperazin-1-yl)-2H-[1,2,4]triazine-3,5-dione

Product 2

HCID 582697662,4-dimethyl-6-[3-oxo-4-(2-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 77%

Procedure

The compound 53 (solid) is prepared from 2-trifluoromethyl-benzoyl chloride and from the intermediate 12b according to the synthesis method 2 under the operating conditions described for Example 40 (yield: 77%).

Workup

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

Sources & evidence

ORD record
ord-ac03d22165ba44bbb08a8d2fbb7ec138
Source dataset
uspto-grants-2013_12
Patent number
US08618287B2

Reaction notes

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