Acetic Acid → HCID 58267987, compound

To a solution of 6-formyl-2-pyridinecarboxylic acid (available from Chemstep Product List, 250 mg, 1.65 mmol) in dichloromethane (6.8 ml) was added morpholine (0.377 ml, 4.31 mmol) and acetic acid (0.083 ml). The mixture was stirred at room temperature for 15 min when sodium triacetoxyborohydride (459 mg, 2.17 mmol) was added and the mixture stirred overnight. The crude reaction mixture was diluted with dichloromethane (10 ml) and methanol was added until a clear solution was observed. The mixture was loaded onto an aminopropyl cartridge (5 g) pre-eluted with dichloromethane. The cartridge was eluted with dichloromethane followed by methanol and fractions containing product were combined and blown to dryness under a stream of nitrogen. The crude product was taken up in sodium hydroxide solution (2M, 25 ml) and washed with dichloromethane (2×25 ml). The aqueous layer was acidified to pH7 using hydrochloric acid (5M) and concentrated under vacuum to approximately 25 ml. The solution was loaded onto an Oasis cartridge (6 g), which had been pre-eluted with methanol (1 volume) followed by water (1 volume). The cartridge was eluted with water (1 volume) followed by methanol. Fractions containing product were combined and dried to give the title compound (129 mg).

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
6. additioncontaining product
7. washwashed with dichloromethane (2×25 ml)
8. concentrationconcentrated under vacuum to approximately 25 ml
9. washhad been pre-eluted with methanol (1 volume)
10. washThe cartridge was eluted with water (1 volume)
11. additionFractions containing product
12. customdried

ORD record

ord-9d97a74fa68b46888ebd7fbfba59de6c

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765743B2