Water → 4-(2,1,3-Benzooxadiazol-4-yl)-N-(2-methoxyethyl)-N-methyl-5-(6-phenylpyridin-3-yl)-4H-1,2,4-triazol-3-ylamine

HRID 1797119Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH3:6].O.Br[C:9]1[N:13]([C:14]2[C:22]3[C:18](=[N:19][O:20][N:21]=3)[CH:17]=[CH:16][CH:15]=2)[C:12]([C:23]2[CH:24]=[N:25][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:27][CH:28]=2)=[N:11][N:10]=1>C(Cl)(Cl)Cl>[N:19]1[O:20][N:21]=[C:22]2[C:14]([N:13]3[C:12]([C:23]4[CH:24]=[N:25][C:26]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)=[CH:27][CH:28]=4)=[N:11][N:10]=[C:9]3[N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH3:6])=[CH:15][CH:16]=[CH:17][C:18]=12

Participants

Conditions

Temperature: 160 °C

Procedure

In a sealed tube, N-(2-methoxyethyl)methylamine (3 ml) and water (3 ml) were added to 4-[3-bromo-5-(6-phenylpyridin-3-yl)-4H-1,2,4-triazol-4-yl]-2,1,3-benzooxadiazol (336 mg) prepared in the Production Example 5, and stirred at 160° C. for 6 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 solid was recrystallized from ethyl acetate, to afford the entitled compound as white crystal (66 mg, 19%). The physico-chemical values are as follows.

Workup

customprepared in the Production Example 5
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
customthe resulting solid was recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-7157820c5458432da9f5fd8f7048482c
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07034047B2

Reaction notes

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