7-(4-chlorophenyl)-8-(4-methoxyphenyl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one → 4-(8-(4-Methoxyphenyl)-3-oxo-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyridin-7-yl)benzonitrile

HRID 2101304Notes

Reaction equation

HRID 2101304 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]3[C:14](=[O:28])[N:15]([CH2:17][C:18]4[CH:19]=[N:20][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:23]=4)[N:16]=[C:10]3[C:9]=2[C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)=[CH:4][CH:3]=1.[C:37]([Cu])#[N:38]>CN1CCCC1=O>[CH3:36][O:35][C:32]1[CH:33]=[CH:34][C:29]([C:9]2[C:10]3[N:11]([C:14](=[O:28])[N:15]([CH2:17][C:18]4[CH:19]=[N:20][C:21]([C:24]([F:25])([F:26])[F:27])=[CH:22][CH:23]=4)[N:16]=3)[CH:12]=[CH:13][C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([C:37]#[N:38])=[CH:3][CH:4]=2)=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 160049417-(4-chlorophenyl)-8-(4-methoxyphenyl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-oneHCID 178418546HCID 178418546, compound

Product 1

HCID 160049424-(8-(4-Methoxyphenyl)-3-oxo-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyridin-7-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
250 °C

Procedure

Into a microwave reaction vial were placed 7-(4-chlorophenyl)-8-(4-methoxyphenyl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (51 mg, 0.10 mmol), CuCN (89.5 mg, 1.0 mmol), and 1-methylpyrrolidin-2-one (1.0 mL, dry). This mixture was heated to 250° C. in a microwave reactor for 8 h. HPLC/MS analysis indicated 55% conversion to desired product. The reaction mixture was cooled to room temperature and poured into 10% aqueous ammonium hydroxide solution. The resulting mixture was stirred at room temperature for 1 h. Solid was filtered off and purified by reverse phase preparative HPLC (without TFA). The title compound (8.6 mg) was obtained as a light yellow solid. HPLC/MS: retention time=3.5 min, [M+H]+=502.

Sources & evidence

ORD record
ord-58c2bb746a85487386a3b73e4e31b117
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Reaction notes

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