3-Bromopropylamine hydrobromide → HCID 178523266, compound

Participants

Reaction Steps

To a solution of 500 mg (2.78 mmol) of 3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid, 682 mg (3.05 mmol) of 3-bromopropylamine hydrobromide, and 1.4 mL (1.04 g, 8.04 mmol) of N,N-diisopropylethylamine in 20 mL of dichloromethane were added 1.2 g (3.06 mmol) of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) and 459 mg (3.38 mmol) of 1-hydroxy-7-azabenzotriazole (HOAT). After being stirred at room temperature for 45 min, the reaction mixture was partitioned between dichloromethane and saturated sodium carbonate aqueous solution. The organic phase was washed with 5% aqueous citric acid solution, then dried over sodium sulfate, and concentrated. The residue was leached with dichloromethane containing a little methanol. Concentration of the organic extract yielded the title compound. LC-MS 300, 302 (M+1).

Provenance & Evidence