Acetic Acid → 5-Fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide acetate

11.1 g (41.07 mmol) of 5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile (Example 8A) were added to 2.22 g (41.07 mmol) of sodium methoxide in methanol (270 ml), and the mixture was stirred at RT for 2 h. 2.64 g (49.29 mmol) of ammonium chloride and acetic acid (9.17 ml) were then added, and the mixture was heated at reflux overnight. The mixture was then concentrated to dryness and the residue was taken up in water (100 ml) and ethyl acetate (100 ml) and adjusted to a pH of 10 using 2N aqueous sodium hydroxide solution. The mixture was stirred intensively at RT for about 1 h. The resulting suspension was filtered with suction and the filter product was washed with ethyl acetate (100 ml), with water (100 ml) and once more with ethyl acetate (100 ml). The residue was dried under high vacuum over phosphorus pentoxide.

1. temperaturethe mixture was heated
2. temperatureat reflux overnight
3. concentrationThe mixture was then concentrated to dryness
4. stirringThe mixture was stirred intensively at RT for about 1 h
5. filtrationThe resulting suspension was filtered with suction
6. washthe filter product was washed with ethyl acetate (100 ml), with water (100 ml) and once more with ethyl acetate (100 ml)
7. dry with materialThe residue was dried under high vacuum over phosphorus pentoxide

ORD record

ord-ce1dcceac5074b64b08a507547b33c93

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921377B2