Hydrochloric Acid → HCID 178505516, compound

HRID 1188118Notes

Reaction equation

HRID 1188118 reaction equation
[CH2:1]([NH:8][C:9]1[N:14]=[C:13]([NH:15][C:16]([C:18]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[N:20](C3CCCCO3)[N:19]=2)=O)[CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.Cl>C1COCC1>[CH2:1]([NH:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([NH:15][CH2:16][C:18]2[CH:22]=[C:21]([C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)[NH:20][N:19]=2)[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 59408767HCID 59408767, compound

Product 1

HCID 178505516HCID 178505516, compoundYield 14.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Boran dimethylsufide (50 μL) was added to a solution of N-(6-(benzylamino)pyridin-2-yl)-5-(4-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxamide 4 (180 mg, 0.38 mmol) in THF (10 ml). The reaction mixture was refluxed over night and cooled. MeOH was added, followed by conc. HCl and the reaction mixture was heated for 5 hrs. Then the reaction mixture was concentrated in vacuum, diluted with water (5 ml) and extracted with chloroform (50 ml×2). The combined organic layers were washed with water and brine, then dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified on silica gel (50% EtOAc: pet-ether) to give N2-benzyl-N6-((5-(4-fluorophenyl)-1H-pyrazol-3-yl)methyl)pyridine-2,6-diamine 5 (20 mg) as an oily material, which was treated with methanolic hydrochloric acid for 2 hrs. The solvent was evaporated under reduced pressure to give a gummy material (20 mg).

Workup

  1. temperatureThe reaction mixture was refluxed over night
  2. temperaturecooled
  3. temperaturethe reaction mixture was heated for 5 hrs
  4. concentrationThen the reaction mixture was concentrated in vacuum
  5. additiondiluted with water (5 ml)
  6. extractionextracted with chloroform (50 ml×2)
  7. washThe combined organic layers were washed with water and brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was purified on silica gel (50% EtOAc: pet-ether)

Sources & evidence

ORD record
ord-774af19ace6846a59f275d47a4cc1055
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

Loading…