Benzylamine → 3-[4-Amino-6-(methyl-phenyl-amino)-[1,3,5]triazin-2-yl]-[1,2,4]oxadiazole-5-carboxylic acid benzylamide

HRID 341415Notes

Reaction equation

HRID 341415 reaction equation
C(O[C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[N:16]=[C:15]([NH2:17])[N:14]=[C:13]([N:18]([CH3:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:12]=2)[N:7]=1)=[O:5])C.[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(O)C>[CH2:26]([NH:33][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[N:16]=[C:15]([NH2:17])[N:14]=[C:13]([N:18]([CH3:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:12]=2)[N:7]=1)=[O:5])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 66803067Ethyl 3-{4-amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazole-5-carboxylate

Product 1

HCID 569411173-[4-Amino-6-(methyl-phenyl-amino)-[1,3,5]triazin-2-yl]-[1,2,4]oxadiazole-5-carboxylic acid benzylamideYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-[4-Amino-6-(methyl-phenyl-amino)-[1,3,5]triazin-2-yl]-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester (prepared in an analogous manner to Example 73, Example 73, 80 mg, 230 μmol), benzylamine (50 μL, 230 μmol) and ethanol (4 mL) were heated under reflux for 4 h. After evaporation of the solvent, the crude residue was loaded onto a 5 g isolute pre-pack silica column in a minimal amount of DCM and eluted with 10-30% ethyl acetate-heptane to give the title compound (79 mg, 85%).

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 4 h
  3. customAfter evaporation of the solvent
  4. washeluted with 10-30% ethyl acetate-heptane

Sources & evidence

ORD record
ord-5b0303eb0f314f27a52587067d3f9701
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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