4-(Methylthio)aniline → 5-methyl-N-[4-(methylthio)phenyl]-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine

HRID 2375014Notes

Reaction equation

HRID 2375014 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][S:40][C:41]1[CH:47]=[CH:46][C:44]([NH2:45])=[CH:43][CH:42]=1>C(O)C>[CH3:1][C:2]1[N:3]=[C:4]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:5]2[C:10]=1[CH:9]=[N:8][C:7]([NH:45][C:44]1[CH:46]=[CH:47][C:41]([S:40][CH3:39])=[CH:42][CH:43]=1)=[N:6]2

Participants

5

Reactant 3

HCID 660384-(Methylthio)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 111522145-methyl-N-[4-(methylthio)phenyl]-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amineYield 50.8%

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), 4-(methylthio)aniline (0.022 mL, 0.17 mmol) and ethanol (2.5 mL) to afford 5-methyl-N-[4-(methylthio)phenyl]-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine (30 mg) as a yellow solid. MS m/z 348 (M+1).

Sources & evidence

ORD record
ord-338acdcf23ff4d42a0767d175d1d7585
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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