Triethylamine → HCID 10001882, compound

Participants

Reaction Conditions

Reaction Steps

680 mg (1.88 mmol) of 1-(2,3-difluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide hydrochloride from Example 28 A and 358 mg (2.07 mmol) of 4-[(dimethylamino)methylene]pyridineacetonitrile from Example 32 A are suspended in a 3:1 benzyl alcohol:isobutanol mixture at RT. Then 38.1 mg (0.38 mmol) of triethylamine are added, and the mixture is stirred at 87–90° C. overnight. A further 0.5 eq. of 4-[(dimethylamino)methylene]pyridineacetonitrile from Example 32 A is added, and the mixture is stirred at 87–90° C. for a further 6 hours. It is diluted with 3 ml of benzyl alcohol and 19 ml of isobutanol and briefly heated at 113° C. It is filtered hot, and the filtrate is slowly cooled while stirring. The solvent is then removed in vacuo, and the product is absorbed on silica gel. It is chromatographed (mobile phase: dichloromethane:methanol 30:1-20:1). The combined pure fractions are recombined and purified by preparative RP-HPLC.

Provenance & Evidence