Hydrochloric Acid → HCID 57500566, compound

Participants

Reaction Steps

2-Methylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid (0.31 g) was suspended in tetrahydrofuran (7 ml), and N,N-dimethylformamide (0.04 ml) was added thereto. A solution of oxalyl chloride (200 μl) in tetrahydrofuran (0.8 ml) was added dropwise thereto with ice cooling, and the mixture was stirred for 1 hour at the same temperature and then stirred for 2 hours at room temperature. Potassium carbonate (0.54 g) was added thereto at −60° C. or less, and then a solution of 1-(aminomethyl)cyclopentylamine (0.22 g) in tetrahydrofuran (0.8 ml) was added dropwise thereto. The mixture was stirred for 30 minutes at −60° C. or less and then stirred for 22 hours at room temperature. Water (6 ml) was added thereto on an ice bath, and the reaction mixture was adjusted to pH 2 by 6 N hydrochloric acid. The reaction mixture was washed with chloroform, and the aqueous phase was adjusted to pH 12 by 5 N sodium hydroxide solution and extracted with chloroform. The resulting product was washed with a saturated saline solution and then dried over sodium sulfate anhydrous. The product was concentrated under reduced pressure to give the title compound (57 mg, Y.:12%).

Provenance & Evidence