Isobutyramide → HCID 86717526, compound

A mixture of 2-methylpropanamide (71.4 mg, 0.820 mmol) and triethyloxonium tetrafluoroborate (154 mg, 0.812 mmol) in THF (2 mL) was stirred at room temperature for 2 h. The solvent was removed and the residue dissolved in ethanol (0.5 mL) and added to a suspension of {(2R,5S)-5-[(6-aminothieno[3,2-b]pyridin-7-yl)amino]tetrahydro-2H-pyran-2-yl}methanol (69.2 mg, 0.248 mmol) in ethanol (1.7 mL). The mixture was stirred at 80° C. for 1 h. The reaction mixture was cooled to room temperature, diluted with methanol, and purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min) to give the desired product. LCMS calculated for C17H22N3O2S (M+H)+: m/z=332.1. Found: 332.1.

1. customThe solvent was removed
2. dissolutionthe residue dissolved in ethanol (0.5 mL)
3. stirringThe mixture was stirred at 80° C. for 1 h
4. temperatureThe reaction mixture was cooled to room temperature
5. custompurified with prep-LCMS (XBridge C18 column
6. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min)

ORD record

ord-6c527d7d6a9645ed989bdcafc9199b7c

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181271B2