Hydrochloride methanol → HCID 67448293, compound

To tert-butyl [(1S)-2-({1-[5-(cyclopropylmethoxy)[1,3]oxazolo[5,4-c]pyridin-2-yl]piperidin-4-yl}oxy)-1-methylethyl]carbamate (328 mg) was added 2M hydrogen chloride/methanol (4 mL), and the mixture was stirred at room temperature for 10 min and concentrated. Pyridine (4 mL) and acetic anhydride (0.5 mL) were added to the residue, and the mixture was stirred at room temperature for 5 min. The reaction mixture was concentrated, saturated brine was added to the residue, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (methanol/ethyl acetate). The obtained solid was washed with diisopropyl ether to give the title compound (197 mg).

1. concentrationconcentrated
2. additionPyridine (4 mL) and acetic anhydride (0.5 mL) were added to the residue
3. stirringthe mixture was stirred at room temperature for 5 min
4. concentrationThe reaction mixture was concentrated
5. additionsaturated brine was added to the residue
6. extractionthe mixture was extracted with ethyl acetate
7. washThe obtained organic layer was washed with saturated brine
8. dry with materialdried over anhydrous magnesium sulfate
9. customThe solvent was evaporated under reduced pressure
10. customthe obtained residue was purified by silica gel column chromatography (methanol/ethyl acetate)
11. washThe obtained solid was washed with diisopropyl ether

ORD record

ord-b537a1431cf340039a21506b8f249944

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703758B2