Piperidine → 2-N-Phenyl-6-[5-(piperidin-1-yl)-1,2,4-oxadiazol-3-yl]-1,3,5-triazine-2,4-diamine

HRID 341426Notes

Reaction equation

HRID 341426 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7]1([NH:13][C:14]2[N:19]=[C:18]([NH2:20])[N:17]=[C:16]([C:21]3[N:25]=[C:24](C(Cl)(Cl)Cl)[O:23][N:22]=3)[N:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>O1CCOCC1>[C:7]1([NH:13][C:14]2[N:19]=[C:18]([NH2:20])[N:17]=[C:16]([C:21]3[N:25]=[C:24]([N:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)[O:23][N:22]=3)[N:15]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 668025602-N-phenyl-6-[5-(trichloromethyl)-1,2,4-oxadiazol-3-yl]-1,3,5-triazine-2,4-diamine2×

Product 1

HCID 668022302-N-Phenyl-6-[5-(piperidin-1-yl)-1,2,4-oxadiazol-3-yl]-1,3,5-triazine-2,4-diamineYield 26%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Piperidine (0.483 mL, 4.902 mmol) was added to a solution of 2-N-phenyl-6-[5-(trichloromethyl)-1,2,4-oxadiazol-3-yl]-1,3,5-triazine-2,4-diamine (prepared in an analogous manner to Intermediate 134, 0.913 g, 2.451 mmol) in dioxane (4 mL) at room temperature. The reaction mixture was stirred at room temperature for two days before being concentrated. The resulting residue was dissolved in EtOAc and water, and washed successively with 1M aq. HCl and brine. The organic phase was dried over sodium sulfate, filtered and concentrated. The crude compound was purified by flash chromatography (heptane:EtOAc 3:2) to afford the title compound (100 mg, 26%).

Workup

  1. concentrationbefore being concentrated
  2. dissolutionThe resulting residue was dissolved in EtOAc
  3. washwater, and washed successively with 1M aq. HCl and brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude compound was purified by flash chromatography (heptane:EtOAc 3:2)

Sources & evidence

ORD record
ord-96ac1341b72b497e8f54660134d23fd4
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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