p-Toluenesulfonic acid → 5-methyl-N-[4-(methyloxy)phenyl]-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine

HRID 2375022Notes

Reaction equation

HRID 2375022 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:46]=[CH:45][C:44]([NH2:47])=[CH:43][CH:42]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCCC1>[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]([NH:47][C:44]1[CH:45]=[CH:46][C:41]([O:40][CH3:39])=[CH:42][CH:43]=1)=[N:6]2

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 7732P-AnisidineHCID 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 445897295-methyl-N-[4-(methyloxy)phenyl]-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amineYield 23.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-methyl-2-(methylthio)-7-phenylimidazo[5,1-f][1,2,4]triazine (Intermediate 72) (75 mg, 0.26 mmol), p-anisidine (32 mg, 0.26 mmol) and p-toluenesulfonic acid (5 mg, 0.03 mmol) in tetrahydrofuran (5 mL) was stirred at reflux overnight. The mixture was then reduced under vacuum, and purified by chromatography on silica gel eluting with 40% ethyl acetate in petrol to give a solid which was purified further by trituration with diethyl ether to afford 5-methyl-N-[4-(methyloxy)phenyl]-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine (20 mg) as a yellow solid. MS m/z 332 (M+1).

Workup

  1. temperatureat reflux overnight
  2. custompurified by chromatography on silica gel eluting with 40% ethyl acetate in petrol
  3. customto give a solid which
  4. customwas purified further by trituration with diethyl ether

Sources & evidence

ORD record
ord-88e2f0a548fc4ef6a869887740058b12
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

Loading…