Water → 4-[3-(4-Methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-ylamino]-benzonitrile

HRID 424402Notes

Reaction equation

HRID 424402 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]2=[N:23][N:24]=[C:25]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[N:15]2[N:14]=1.O>CN(C)C=O>[CH3:33][O:32][C:29]1[CH:30]=[CH:31][C:26]([C:25]2[N:15]3[N:14]=[C:13]([NH:1][C:2]4[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=4)[C:22]4[C:17]([C:16]3=[N:23][N:24]=2)=[CH:18][CH:19]=[CH:20][CH:21]=4)=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 133964-AminobenzonitrileHCID 24758Sodium hydrideHCID 7126896-Chloro-3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazine2×

Product 1

HCID 115673374-[3-(4-Methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-ylamino]-benzonitrileYield 84.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

295 mg of 4-amino-benzonitrile and 6 mg of sodium hydride (60%) in 2.5 ml of N,N-dimethylformamide are treated with 100 mg of 6-chloro-3-(4-methoxy-phenyl)-[1,2,4]triazolo[3,4-a]phthalazine (compound B1) at ambient temperature. After 10 min the reaction mixture is added to water, the precipitate is filtered with suction and the solid is recrystallized from N,N-dimethylformamide to yield 107 mg of the title compound.

Workup

  1. filtrationthe precipitate is filtered with suction
  2. customthe solid is recrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-59f0af71099a4577b87e2e3d544a1fd0
Source dataset
uspto-grants-2012_01
Patent number
US08106047B2

Reaction notes

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