Potassium Carbonate → N-[2-(4-Bromophenyl)-5,7-dimethylimidazo[5,1-f][1,2,4]triazin-4-yl]-N-(3,4,5-tri-methoxyphenyl)amine

HRID 1270309Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([N:14]3[CH:18]=NC=N3)[C:11]3=[C:19]([CH3:23])[N:20]=[C:21]([CH3:22])[N:10]3[N:9]=2)=[CH:4][CH:3]=1.[CH3:24][O:25][C:26]1[CH:27]=C([CH:30]=[C:31]([O:35][CH3:36])[C:32]=1[O:33][CH3:34])N.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([NH:14][C:18]3[CH:27]=[C:26]([O:25][CH3:24])[C:32]([O:33][CH3:34])=[C:31]([O:35][CH3:36])[CH:30]=3)[C:11]3=[C:19]([CH3:23])[N:20]=[C:21]([CH3:22])[N:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 4.0 g (10.80 mmol) of 2-(4-bromophenyl)-5,7-dimethyl-4-(1H-1,2,4-triazol-1-yl)imidazo[5,1-f][1,2,4]triazine from example 13A in DMF is treated with 2.97 g (16.21 mmol) of 3,4,5-trimethoxyaniline and 2.24 g (16.21 mmol) of potassium carbonate. The reaction mixture is stirred overnight at 90° C. After cooling, the solvent is removed on a rotary evaporator, the residue is treated twice more with toluene and the toluene is stripped off again. The crude product is extracted by stirring with a little methanol and filtered off with suction.

Workup

temperatureAfter cooling
customthe solvent is removed on a rotary evaporator
additionthe residue is treated twice more with toluene
extractionThe crude product is extracted
stirringby stirring with a little methanol
filtrationfiltered off with suction

Sources & evidence

ORD record: ord-5ddc2ae9ee904629825075824a6affe8
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07202243B2

Reaction notes

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