Acetic Acid → HCID 58268016, compound

HRID 1615982Notes

Reaction equation

HRID 1615982 reaction equation
[CH:1]([C:3]1[N:8]=[C:7]([C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=1)=O.[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.CO>[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([CH2:1][C:3]2[N:8]=[C:7]([C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=2)[CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 140613846-Formylpyridine-2-carboxylic acid

Product 1

HCID 58268016HCID 58268016, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-formyl-2-pyridinecarboxylic acid [Chemstep Product List] (0.25 g) in dichloromethane (6.8 ml) was added 1-methylpiperazine (0.481 ml) and acetic acid (0.083 ml). The mixture was stirred at room temperature for 15 min when sodium triacetoxyborohydride (0.459 g) was added and the mixture stirred overnight. The crude reaction mixture was diluted with dichloromethane (60 ml) and methanol was added until a clear solution was observed. The mixture was loaded onto an aminopropyl-SPE cartridge (5 g) pre-eluted with dichloromethane. The cartridge was eluted with dichloromethane and methanol and fractions containing product were combined and blown to dryness under a stream of nitrogen. The crude product was taken up in dichloromethane (2×25 ml) and washed with 2M sodium hydroxide solution (25 ml). The aqueous layer was acidified to pH7 using 5N hydrochloric acid and concentrated under vacuum to approximately 25 ml. The solution was loaded onto an Oasis cartridge (6 g) and eluted with water (one volume) and methanol. Fractions containing product were combined and dried to give the title compound (0.171 g).

Workup

  1. additionwas added
  2. customThe crude reaction mixture
  3. additionwas added until a clear solution
  4. washpre-eluted with dichloromethane
  5. washThe cartridge was eluted with dichloromethane and methanol and fractions
  6. additioncontaining product
  7. washwashed with 2M sodium hydroxide solution (25 ml)
  8. concentrationconcentrated under vacuum to approximately 25 ml
  9. washeluted with water (one volume) and methanol
  10. additionFractions containing product
  11. customdried

Sources & evidence

ORD record
ord-42e2147d89af404ebb09e92e916f6926
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

Loading…