Hydrochloric Acid → HCID 25001112, compound

HRID 1188115Notes

Reaction equation

HRID 1188115 reaction equation
[CH2:1]([NH:8][C:9]1[CH:24]=[CH:23][C:12]([C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][N:17]=2)=O)=[CH:11][N: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:24]=[CH:23][C:12]([CH2:13][NH:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][N:17]=2)=[CH:11][N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 59408783HCID 59408783, compound

Product 1

HCID 25001112HCID 25001112, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

BMS (400 μL) was added to a solution of 6-(benzylamino)-N-(5-fluoropyridin-2-yl)nicotinamide 4 in THF (20 mL). The reaction mixture was refluxed for 16 hrs. Then the reaction mixture was cooled to RT. MeOH (2 mL), followed by conc. HCl were added. The reaction mixture was refluxed for 8 hrs, concentrated and diluted with water (2 mL). The pH was adjusted to 14 and the reaction mixture was extracted with chloroform (50 mL×2). All organic phases were washed with brine and dried over Na2SO4. Evaporation of the solvent gave a crude product which was purified on silica gel (1:1, EtOAc: Pet-ether) to give N-benzyl-5-((5-fluoropyridin-2-ylamino)methyl)pyridin-2-amine 5. This was treated with HCl/MeOH to give the corresponding salt (50 mg 13%) as a white solid. Mp. 166-168° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 hrs
  2. additionwere added
  3. temperatureThe reaction mixture was refluxed for 8 hrs
  4. concentrationconcentrated
  5. additiondiluted with water (2 mL)
  6. extractionthe reaction mixture was extracted with chloroform (50 mL×2)
  7. washAll organic phases were washed with brine
  8. dry with materialdried over Na2SO4
  9. customEvaporation of the solvent
  10. customgave a crude product which
  11. customwas purified on silica gel (1:1, EtOAc: Pet-ether)

Sources & evidence

ORD record
ord-20cf82448733458484dc5b1fb6f565ab
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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