(2-Methoxyethyl)(methyl)amine → [4-(2-Bromophenyl)-5-(6-phenylpyridin-3-yl)-4H-1,2,4-triazol-3-yl]-N-(2-methoxyethyl)-N-methylamine

HRID 1797117

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH3:6].Br[C:8]1[N:9]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Br:31])[C:10]([C:13]2[CH:14]=[CH:15][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:17][CH:18]=2)=[N:11][N:12]=1>C(Cl)(Cl)Cl>[Br:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[N:9]1[C:10]([C:13]2[CH:18]=[N:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)=[N:11][N:12]=[C:8]1[N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH3:6]

Participants

Conditions

Temperature: 200 °C

Procedure

In a sealed tube, N-(2-methoxyethyl)methylamine (3 ml) was added to 5-[5-bromo-4-(2-bromophenyl)-4H-1,2,4-triazol-3-yl]-2-phenylpyridine (1.0 g) prepared in the Production Example 3, and stirred at 180° C. for 13 hours and at 200° C. for 24 hours. After the reaction solution was cooled to ambient temperature, chloroform was added to the solution, which was then washed with saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the resulting residue was washed with ethyl acetate, to afford the entitled compound as white solid (711 mg, 70%). The physico-chemical values are as follows.

Workup

customprepared in the Production Example 3
temperatureAfter the reaction solution was cooled to ambient temperature
washwas then washed with saturated aqueous sodium hydrogen carbonate solution
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
customAfter the solvent was evaporated under reduced pressure
washthe resulting residue was washed with ethyl acetate

Sources & evidence

ORD record: ord-7ae3865481ac4fea8fe65ac34f5a355a
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07034047B2

Linked notes

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