HCID 178432500, compound → 2-Amino-5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin

HRID 2374938Notes

Reaction equation

HRID 2374938 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:5]2[C:10]=1[CH2:9][NH:8][C:7]([NH2:11])=[N:6]2>CCO.[Pd]>[CH3:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=2)[N:5]2[C:10]=1[CH:9]=[N:8][C:7]([NH2:11])=[N:6]2

Participants

4

Reactant 1

HCID 178432500HCID 178432500, compound2×

Product 1

HCID 587120012-Amino-5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazinYield 38.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mechanical mixture of 5-methyl-7-[3-(trifluoromethyl)phenyl]-3,4-dihydroimidazo[5,1-f][1,2,4]triazin-2-amine (Intermediate 44) (1.30 g, 4.41 mmol) and Pd/C (0.50 g) in EtOH (250 mL) was heated at reflux for 7 days. The reaction mixture was then cooled to rt and filtered through celite. Concentration of the filtrate followed by purification of the residue by chromatography afforded 5-methyl-7-[3-(trifluoromethyl)phenyl]-imidazo[5,1-f][1,2,4]triazin-2-amine (0.50 g) as a pale yellow solid. 1H NMR (Acetone-d6): δ9.06 (s, 1H), 8.94 (s, 1H), 8.92-8.86 (m, 1H), 7.75-7.69 (m, 2H), 6.29 (bs, 2H), 2.55 (s, 3H). MS m/z 292 (M−1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 7 days
  3. filtrationfiltered through celite
  4. customConcentration of the filtrate followed by purification of the residue by chromatography

Sources & evidence

ORD record
ord-b277feaaf1144bdda375829a7b1a45ab
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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