Methanol → HCID 35028755, compound

The product obtained in 116a (550 mg, 2.74 mmol) in 5 mL THF was added to a mixture of 2-amino-4-methyl-pyridine (750 mg, 6.94 mmol) in 10 mL THF under stirring at ambient temperature. The mixture was stirred for 20 min at ambient temperature, then 1 mL methanol was added and the mixture was concentrated i.vac. The residue was purified by HPLC (C18 symmetry, eluent-gradient: (water+0.15% HCOOH)/acetonitrile=90:10->0:100). Conc. ammonia (aq) was added to the product containing fractions until alkaline, and acetonitrile was removed by evaporation. The aqueous mixture was extracted with dichloromethane/methanol 9:1, the combined organic layers dried over MgSO4 and concentrated to dryness i. vac. and the residue triturated with methanol. After filtration, the solid was washed with methanol and dried at 55° C.

1. stirringThe mixture was stirred for 20 min at ambient temperature
2. concentrationthe mixture was concentrated i.vac
3. customThe residue was purified by HPLC (C18 symmetry, eluent-gradient: (water+0.15% HCOOH)/acetonitrile=90:10->0:100)
4. additionConc. ammonia (aq) was added to the product
5. additioncontaining fractions until alkaline, and acetonitrile
6. customwas removed by evaporation
7. extractionThe aqueous mixture was extracted with dichloromethane/methanol 9:1
8. dry with materialthe combined organic layers dried over MgSO4
9. concentrationconcentrated to dryness i
10. customand the residue triturated with methanol
11. filtrationAfter filtration
12. washthe solid was washed with methanol
13. customdried at 55° C.

ORD record

ord-2f46f1b6b6074872864ff3c96259535b

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916599B2