Water → HCID 178474433, compound

HRID 241453Notes

Reaction equation

HRID 241453 reaction equation
Br[CH:2]([CH3:14])[C:3]([C:5]1[CH:6]=[N:7][C:8]([CH:11]([F:13])[F:12])=[CH:9][CH:10]=1)=O.[C:15]([NH:18][C:19]([NH2:21])=[NH:20])(=[O:17])[CH3:16].O>CN(C=O)C>[F:12][CH:11]([F:13])[C:8]1[N:7]=[CH:6][C:5]([C:3]2[NH:21][C:19]([NH:18][C:15](=[O:17])[CH3:16])=[N:20][C:2]=2[CH3:14])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 86674204HCID 86674204, compoundHCID 178475102HCID 178475102, compound

Product 1

HCID 178474433HCID 178474433, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Dissolve 2-bromo-1-[6-(difluoromethyl)-3-pyridyl]propan-1-one (0.500 g, 1.89 mmol) and acetyl guanidine (0.514 g, 5.68 mmol) in DMF (12 mL). Heat the mixture to 50° C., and stir for 16 hours. Pour the mixture into water, and extract with EtOAc (3×20 mL). Dry the combined organic extracts over sodium sulfate; filter; collect the filtrate; and concentrate the filtrate under reduced pressure. Purify the resulting residue by flash chromatography (silca gel) eluting with a 40:1 ratio of DCM/MeOH to give the title compound as a white solid (0.229 g, 46% yield). LCMS (m/z) 267 (M+1).

Workup

  1. extractionextract with EtOAc (3×20 mL)
  2. dry with materialDry the combined organic extracts over sodium sulfate
  3. filtrationfilter
  4. customcollect the filtrate
  5. concentrationand concentrate the filtrate under reduced pressure
  6. customPurify the resulting residue by flash chromatography (silca gel)
  7. washeluting with a 40:1 ratio of DCM/MeOH

Sources & evidence

ORD record
ord-266aacee16f84e04829bd18de27c27d4
Source dataset
uspto-grants-2014_02
Patent number
US08648200B2

Reaction notes

Loading…