Hydrochloric Acid → HCID 178505516, compound

HRID 1188130Notes

Reaction equation

HRID 1188130 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.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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 21893726Hydrochloride methanolHCID 59408767HCID 59408767, compound

Product 1

HCID 178505516HCID 178505516, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

BMS (2.2 mmol, 165 μL) (400 μL) was added to a solution of 6-bromo-N-(6-bromopyridin-2-yl)nicotinamide 4 (300 mg, 0.73 mmol) in THF (20 ml). The reaction mixture was refluxed for 16 hrs. Then the reaction mixture was cooled to RT, MeOH (2 mL) was added, followed by cone. HCl. and the reaction mixture was refluxed for 8 hrs. The reaction mixture was concentrated and diluted with water (2 ml), the pH adjusted to 14 and the reaction mixture was extracted with chloroform (50 ml×2). The combined organic phases were washed with brine, dried over Na2SO4. Evaporation of the solvent gave a crude product that was purified on silica gel (1:1, EtOAc: pet-ether) to give a white solid which was treated with MeOH/HCl to give N2-((6-(benzylamino)pyridin-3-yl)methyl)pyridine-2,6-diamine 5, hydrochloride salt (50 mg, 49%) as a white solid. Mp. 261-262° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 hrs
  2. temperatureand the reaction mixture was refluxed for 8 hrs
  3. concentrationThe reaction mixture was concentrated
  4. additiondiluted with water (2 ml)
  5. extractionthe reaction mixture was extracted with chloroform (50 ml×2)
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over Na2SO4
  8. customEvaporation of the solvent
  9. customgave a crude product that
  10. customwas purified on silica gel (1:1, EtOAc: pet-ether)
  11. customto give a white solid which

Sources & evidence

ORD record
ord-00ec0773b0af48f3b066713434f2c1d3
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

Loading…