4-[2-(Dimethylamino)ethoxy]aniline → N-(4-{[2-(dimethylamino)ethyl]oxy}-phenyl)-5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine

HRID 2375015Notes

Reaction equation

HRID 2375015 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.[NH2:39][C:40]1[CH:45]=[CH:44][C:43]([O:46][CH2:47][CH2:48][N:49]([CH3:51])[CH3:50])=[CH:42][CH:41]=1>C(O)C>[CH3:50][N:49]([CH3:51])[CH2:48][CH2:47][O:46][C:43]1[CH:44]=[CH:45][C:40]([NH:39][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:41][CH:42]=1

Participants

5

Reactant 3

HCID 64846554-[2-(Dimethylamino)ethoxy]anilineHCID 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 11372661N-(4-{[2-(dimethylamino)ethyl]oxy}-phenyl)-5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amineYield 24.2%

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), {2-[(4-aminophenyl)oxy]ethyl}dimethylamine (32 mg, 0.17 mmol) and ethanol (2.5 mL) to afford N-(4-{[2-(dimethylamino)ethyl]oxy}-phenyl)-5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine (16 mg) as a yellow solid. MS m/z 389 (M+1).

Sources & evidence

ORD record
ord-6ef7a0e7dc3348faadedbad2a55eb0e7
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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