Diisopropylethylamine → HCID 74222515, compound

Participants

Reaction Conditions

Reaction Steps

750 mg of 8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid Example 3A (2.36 mmol, 1 equivalent) were initially charged in 15 ml of DMF, and 2.24 g of N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminium hexafluorophosphate (HATU, 5.89 mmol, 2.5 equivalents) and 1.03 ml of N,N-diisopropylethylamine (0.76 g, 5.89 mmol, 2.5 equivalents) were added. The mixture was stirred at 60° C. for 20 min, 0.98 g of methyl 3-amino-4,4,4-trifluorobutanoate hydrochloride (Example 22A, 4.71 mmol, 2 equivalents) was added and the mixture was stirred at 60° C. overnight. The mixture was then added to 120 ml of water and stirred at RT for 30 min. The precipitated solid was filtered off, washed with 6 ml of diethyl ether and dried under reduced pressure. The residue was then concentrated on a silica gel column (mobile phases: dichloromethane/ethyl acetate 10:1). This gave 0.32 g (29% of theory) of the title compound.

Provenance & Evidence