Potassium Carbonate → 2-N-Methyl-2-N-phenyl-6-(5-{4-[(2,2,2-trifluoroethoxy)methyl]piperidin-1-yl}-1,2,4-oxadiazol-3-yl)-1,3,5-triazine-2,4-diamine

HRID 341422Notes

Reaction equation

HRID 341422 reaction equation
[CH3:1][N:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:3]1[N:8]=[C:7]([NH2:9])[N:6]=[C:5]([C:10]2[N:14]=[C:13](C(Cl)(Cl)Cl)[O:12][N:11]=2)[N:4]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[F:32][C:33]([F:44])([F:43])[CH2:34][O:35][CH2:36][CH:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1>CN(C=O)C>[CH3:1][N:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:3]1[N:8]=[C:7]([NH2:9])[N:6]=[C:5]([C:10]2[N:14]=[C:13]([N:40]3[CH2:39][CH2:38][CH:37]([CH2:36][O:35][CH2:34][C:33]([F:32])([F:43])[F:44])[CH2:42][CH2:41]3)[O:12][N:11]=2)[N:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 457917814-((2,2,2-Trifluoroethoxy)methyl)piperidine hydrochloride2×HCID 66802564N-methyl-N-phenyl-6-(5-trichloromethyl-[1,2,4]oxadiazol-3-yl)-[1,3,5]triazine-2,4-diamine2×

Product 1

HCID 668024632-N-Methyl-2-N-phenyl-6-(5-{4-[(2,2,2-trifluoroethoxy)methyl]piperidin-1-yl}-1,2,4-oxadiazol-3-yl)-1,3,5-triazine-2,4-diamineYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-N-methyl-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 60, 0.110 g, 0.285 mmol) was added to a mixture of potassium carbonate (0.071 g, 0.518 mmol) in DMF (2 mL) at room temperature and the mixture was stirred for 5 min. 4-[(2,2,2-trifluoroethoxy)methyl]piperidine hydrochloride (Intermediate 179, 0.060 g, 0.259 mmol) was added to the reaction mixture and stirred at room temperature for 2 h. The reaction mixture was concentrated under reduced pressure, dissolved in water and extracted with EtOAc. The combined organic extracts was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude compound was purified by FCC (EtOAc:heptane 1:1) and preparative HPLC, Method A, to afford the title compound (22.1 mg, 18%).

Workup

  1. stirringstirred at room temperature for 2 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutiondissolved in water
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic extracts was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude compound was purified by FCC (EtOAc:heptane 1:1) and preparative HPLC, Method A

Sources & evidence

ORD record
ord-0afeb41b1d6b48d59d838a46f913edc6
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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