Morpholine → 1-(4-fluoro-phenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [1-(6-morpholin-4-yl-pyridin-3-yl)-cyclopropyl]-amide

A solution of 1-(4-fluoro-phenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [1-(6-bromo-pyridin-3-yl)-cyclopropyl]-amide (35 mg, 0.077 mmol) and morpholine (68 μL, 0.77 mmol) in DMSO (1 mL) is heated in a pressure tube at 160° C. After 40 hours, the mixture is cooled to room temperature, diluted with EtOAc (50 mL) and washed with saturated aqueous ammonium chloride (2×50 mL), saturated aqueous sodium bicarbonate (50 mL), brine (50 mL), dried over MgSO4, filtered and concentrated. The resulting solid is purified by silica gel chromatography eluting with a gradient of 0-5% methanol in dichloromethane to give a solid, which is triturated with ether (5 mL), filtered and dried to afford the title compound.

1. washwashed with saturated aqueous ammonium chloride (2×50 mL), saturated aqueous sodium bicarbonate (50 mL), brine (50 mL)
2. dry with materialdried over MgSO4
3. filtrationfiltered
4. concentrationconcentrated
5. customThe resulting solid is purified by silica gel chromatography
6. washeluting with a gradient of 0-5% methanol in dichloromethane
7. customto give a solid, which
8. customis triturated with ether (5 mL)
9. filtrationfiltered
10. customdried

ORD record

ord-8daae4d9bdc645339ec1d543b611e020

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09056858B2