3,5-Dimethoxyaniline → N-[3,5-bis(methyloxy)phenyl]-5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine

HRID 2375012Notes

Reaction equation

HRID 2375012 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:5]2[C:10]=1[CH:9]=[N:8][C:7](SC)=[N:6]2.CC1N=C(C2C=CC=CC=2)N2C=1C=NC(S(C)(=O)=O)=N2.[CH3:39][O:40][C:41]1[CH:42]=[C:43]([CH:45]=[C:46]([O:48][CH3:49])[CH:47]=1)[NH2:44]>C(O)C>[CH3:49][O:48][C:46]1[CH:45]=[C:43]([NH:44][C:7]2[N:8]=[CH:9][C:10]3=[C:2]([CH3:1])[N:3]=[C:4]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[N:5]3[N:6]=2)[CH:42]=[C:41]([O:40][CH3:39])[CH:47]=1

Participants

5

Reactant 3

HCID 663013,5-DimethoxyanilineHCID 534718325-Methyl-2-(methylthio)-7-phenylimidazo[5,1-F][1,2,4]triazineHCID 534718335-Methyl-2-(methylsulfonyl)-7-phenylimidazo[5,1-F][1,2,4]triazine

Product 1

HCID 11302897N-[3,5-bis(methyloxy)phenyl]-5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amineYield 37.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Applying the displacement procedure, using 5-methyl-2-(methylthio)-7-phenylimidazo[5,1-f][1,2,4]triazine (Intermediate 72) (50 mg, 0.17 mmol), 3,5-dimethoxyaniline (26.5 mg, 0.17 mmol) and ethanol (2.5 mL) to afford N-[3,5-bis(methyloxy)phenyl]-5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine (23 mg) as a yellow solid. MS m/z 362 (M+1).

Sources & evidence

ORD record
ord-ed69aba5170046368a327c9cc2154ae5
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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