3-Pyridinecarbonyl chloride, 6-(2,2,2-trifluoroethoxy)- → N-Methyl-N-phenyl-6-{5-[6-(2,2,2-trifluoroethoxy)-pyridin-3-yl]-[1,2,4]oxadiazol-3-yl}-[1,3,5]triazine-2,4-diamine

HRID 341413Notes

Reaction equation

HRID 341413 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]([CH3:16])[C:9]2[CH:14]=[CH:13][CH:12]=[C:11](C)[CH:10]=2)[N:5]=[C:4]([C:17]([NH:19][OH:20])=[NH:18])[N:3]=1.[F:21][C:22]([F:35])([F:34])[CH2:23][O:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=O)=[CH:27][N:26]=1>N1C=CC=CC=1>[CH3:16][N:8]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:6]1[N:7]=[C:2]([NH2:1])[N:3]=[C:4]([C:17]2[N:18]=[C:29]([C:28]3[CH:27]=[N:26][C:25]([O:24][CH2:23][C:22]([F:35])([F:21])[F:34])=[CH:33][CH:32]=3)[O:20][N:19]=2)[N:5]=1

Participants

4

Reactant 2

HCID 235127223-Pyridinecarbonyl chloride, 6-(2,2,2-trifluoroethoxy)-HCID 1784255374-amino-N-hydroxy-6-(methyl-3-methylphenyl-amino)-[1,3,5]triazine-2-carboxamidine2×

Product 1

HCID 66802733N-Methyl-N-phenyl-6-{5-[6-(2,2,2-trifluoroethoxy)-pyridin-3-yl]-[1,2,4]oxadiazol-3-yl}-[1,3,5]triazine-2,4-diamineYield 32%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a sealed tube under nitrogen was placed 4-amino-N-hydroxy-6-(methyl-3-methylphenyl-amino)-[1,3,5]triazine-2-carboxamidine (Intermediate 1, 100 mg, 380 μmol). Then 5 mL anhydrous pyridine was added followed by 6-(2,2,2-trifluoroethoxy)-nicotinoyl chloride (prepared in an analogous manner to Intermediate 57, 91 mg, 380 μmol). The mixture was stirred at room temperature for 48 hrs. After this time the mixture was heated at 115 C for 18 h, allowed to cool and concentrated in vacuo. The crude residue was loaded onto a 2 g isolute silica column in a minimal amount of DCM and eluted with ethyl acetate-heptane 20-50% to give the title compound (54 mg, 32%).

Workup

  1. customIn a sealed tube under nitrogen was placed
  2. temperatureAfter this time the mixture was heated at 115 C for 18 h
  3. temperatureto cool
  4. concentrationconcentrated in vacuo
  5. washeluted with ethyl acetate-heptane 20-50%

Sources & evidence

ORD record
ord-48b1228c1d92429b90d12de62c8d9b72
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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