Hydrochloric Acid → HCID 178509195, compound

HRID 451530Notes

Reaction equation

HRID 451530 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:16][CH2:17][CH2:18][O:19]C2CCCCO2)[C:10]2[NH:14][C:13]([NH2:15])=[N:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].Cl>CO>[NH2:15][C:13]1[NH:14][C:10]([N:9]([C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=2)[CH2:16][CH2:17][CH2:18][OH:19])=[N:11][N:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178509194HCID 178509194, compound

Product 1

HCID 178509195HCID 178509195, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N3-(3,4-difluorophenyl)-N3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-4H-1,2,4-triazole-3,5-diamine (43 mg, 122 μmol) in methanol (1 mL) was added 2 N aqueous hydrogen chloride solution. The solution was stirred at room temperature over night. The solvent was evaporated under reduced pressure and the residue was taken up in saturated aqueous sodium hydrogen carbonate solution. It was extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium hydrogen carbonate solution and with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure to yield the title compound as a white solid (34 mg, quant) without further purification. MS ISP (m/e): 270.3 (100) [(M+H)+].

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionIt was extracted twice with ethyl acetate
  3. washThe combined organic layers were washed with saturated aqueous sodium hydrogen carbonate solution and with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6622dda823bb4bfa851d51779f97e0ad
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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