(4-Fluorophenyl)glyoxal → 4-[[6-(4-Fluorophenyl)-[1,2,4]triazolo[4,3-B][1,2,4]triazin-3-Yl]methyl]phenol

HRID 1244632Notes

Reaction equation

HRID 1244632 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH:9]=O)=[CH:4][CH:3]=1.[NH2:12][N:13]1[C:17]([NH2:18])=[N:16][N:15]=[C:14]1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1>C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[N:18][C:17]3[N:13]([C:14]([CH2:19][C:20]4[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=4)=[N:15][N:16]=3)[N:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 101249(4-Fluorophenyl)glyoxalHCID 219193134-[(4,5-Diamino-4H-1,2,4-triazol-3-yl)methyl]phenol

Product 1

HCID 113246894-[[6-(4-Fluorophenyl)-[1,2,4]triazolo[4,3-B][1,2,4]triazin-3-Yl]methyl]phenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

a mixture of (4-fluoro-phenyl)-oxo-acetaldehyde (72 mg, 0.4 mmol) and 4-(4,5-diamino-4H-[1,2,4]triazol-3-ylmethyl)-phenol (82 mg, 0.4 mmol) in acetic acid was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was purified on a silica gel column (CH2Cl2:EtOAc=2:8, 3:7) to afford two isomers 4-[7-(4-fluoro-phenyl)-[1,2,4]triazolo[4,3-b][1,2,4]triazin-3-ylmethyl]-pheno desired product 4-[6-(4-fluoro-phenyl)-[1,2,4]triazolo[4,3-b][1,2,4]triazin-3-ylmethyl ]phenol (Example 1).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified on a silica gel column (CH2Cl2:EtOAc=2:8, 3:7)

Sources & evidence

ORD record
ord-88c0ee13bdfd4ce6bc276b18beacb8a6
Source dataset
uspto-grants-2006_10
Patent number
US07122548B2

Reaction notes

Loading…