Pyridine → N-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-4-trifluoromethyl-benzamide

HRID 277041Notes

Reaction equation

HRID 277041 reaction equation
[C:1]1([C:7]2[N:22]=[C:10]3[CH:11]=[C:12]([C:16]4[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=4)[CH:13]=[C:14]([NH2:15])[N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[F:29][C:30]([F:41])([F:40])[C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1>ClCCl>[C:1]1([C:7]2[N:22]=[C:10]3[CH:11]=[C:12]([C:16]4[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=4)[CH:13]=[C:14]([NH:15][C:35](=[O:36])[C:34]4[CH:38]=[CH:39][C:31]([C:30]([F:29])([F:40])[F:41])=[CH:32][CH:33]=4)[N:9]3[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 676074-(Trifluoromethyl)benzoyl chloride2×HCID 226297002-Phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Product 1

HCID 9890397N-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-4-trifluoromethyl-benzamideYield 60.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.29 g (0.001 mol) 2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine and 1.13 ml(0.014 mol) pyridine in 30 ml dichloromethane was stirred with 0.63 g(0.003 mol) p-trifluoromethyl benzoyl chloride for 18 hours at room temperature. Then another 0.63 g(0.003 mol) p-trifluoromethyl benzoyl chloride were added and stirring was continued at reflux temperature for 48 hours. After extraction with aqueous sodium hydroxide the organic solvents were distilled off and the residue was recrystallised from methanol to yield 0.28 g(60%) N-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-4-trifluoromethyl-benzamide as white crystals. MS m/e (%): 460 (M+H+, 100).

Workup

  1. temperatureat reflux temperature for 48 hours
  2. extractionAfter extraction with aqueous sodium hydroxide the organic solvents
  3. distillationwere distilled off
  4. customthe residue was recrystallised from methanol

Sources & evidence

ORD record
ord-25b371c57dee49878758e2a82c16bfd3
Source dataset
uspto-grants-2002_03
Patent number
US06355653B1

Reaction notes

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