Water → HCID 178482073, compound

HRID 45850Notes

Reaction equation

HRID 45850 reaction equation
C([N:8](CC1C=CC=CC=1)[C:9]1[C:10]([F:29])=[C:11]([C:16]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:27][CH3:28])[CH:22]=3)=[CH:19][NH:18][N:17]=2)[C:12]([F:15])=[CH:13][CH:14]=1)C1C=CC=CC=1.O>C1(C)C=CC=CC=1>[NH2:8][C:9]1[C:10]([F:29])=[C:11]([C:16]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:27][CH3:28])[CH:22]=3)=[CH:19][NH:18][N:17]=2)[C:12]([F:15])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 962WaterHCID 178482074HCID 178482074, compound

Product 1

HCID 178482073HCID 178482073, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of {4-[3-(3-dibenzylamino-2,6-difluoro-phenyl)-1H-pyrazol-4-yl]-pyridin-2-yl}-methyl-amine (408 mg, 0.849 mmol) in toluene (4.30 mL) trifluoro-methanesulfonic acid (4.30 mL) was added and the mixture was irradiated in the microwave oven at 120° C. for 30 minutes. The reaction was then poured into water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaHCO3 and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography eluting with 5% methanol in methylene chloride (60% over 4 steps).

Workup

  1. customthe mixture was irradiated in the microwave oven at 120° C. for 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified by silica gel column chromatography
  8. washeluting with 5% methanol in methylene chloride (60% over 4 steps)

Sources & evidence

ORD record
ord-cb27cd4fe144455da49fa85844a700ab
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

Loading…