6-(2-chlorophenyl)-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one → 6-(2-chlorophenyl)-7-(4-chlorophenyl)-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

HRID 2101397Notes

Reaction equation

HRID 2101397 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:10][C:11]2[N:12]([C:14](=[O:17])[NH:15][N:16]=2)[CH:13]=1.Cl[CH2:26][C:27]1[C:28]([CH3:37])=[N:29][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:31][CH:32]=1.BrC1C2N(C(=O)N(CC3C(C)=NC(C(F)(F)F)=CC=3)N=2)C(C)=CC=1C1C=CC(Cl)=CC=1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)=[CH:10][C:11]2[N:12]([C:14](=[O:17])[N:15]([CH2:26][C:27]3[C:28]([CH3:37])=[N:29][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:31][CH:32]=3)[N:16]=2)[CH:13]=1

Participants

4

Reactant 3

HCID 577994146-(2-chlorophenyl)-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-oneHCID 577994468-bromo-7-(4-chlorophenyl)-5-methyl-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-oneHCID 598348153-(Chloromethyl)-2-methyl-6-(trifluoromethyl)pyridine

Product 1

HCID 577994366-(2-chlorophenyl)-7-(4-chlorophenyl)-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-oneYield 47.2%

Procedure

The title compound (25 mg, 47% yield) as an off-white solid was prepared from 6-(2-chlorophenyl)-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (36 mg, 0.1 mmol) and 3-(chloromethyl)-2-methyl-6-(trifluoromethyl)pyridine (31 mg, 0.15 mmol) in a manner analogous to that in which 8-bromo-7-(4-chlorophenyl)-5-methyl-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one was prepared. HPLC/MS: retention time=4.30 min, [M+H]+=529.1.

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-99f4300afec844e9bd3cf7989222e274
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Reaction notes

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