Dhruvi Panchal There are multiple reaction conditions that you can try. You could use coupling reagents like PyBOP, HATU, DIC. You can use the additive HOBt (reaction might be totally successful without the usage of HOBt). You can use as a base DIEA or TEA or DMAP in some cases.

You use 1 eq of MnTBAP, 1 eq of PyBOP, and 1 eq of DIEA in anhydrous DMF. You can check with TLC about the activation. In general, it might take from a few mins to a few hours. If TLC is not available, you can let the activation for 3-4 hours. At the same time, you can activate your propargylamine (propargylamine 1eq and DIEA 1 eq in anhydrous DMF). Then, you can add dropwise the propargylamine solution to the MnTBAP solution.

Panchal

A solution of (1 mmol) of the selected acid, 0.38 g (1 mmol) of HATU and 0.35 mL (2 mmol) DIEA in 2 mL DMF was stirred at 0 C. Then 0.31 g (1 mmol) amine was added. The reaction mixture was stirred at 0 C for 1 h and left overnight at room temperature. The reaction mixture was poured into ice water, filtered, washed with 5% aqueous citric acid solution (2  10 mL), saturated sodium bicarbonate solution (2  10 mL) and water. The crude product was recrystallized from suitable solvent

--- European Journal of Medicinal Chemistry 93 (2015) 308-320

[Preparation of compounds 7]

Good Luck

Carboxylic acid-Amine coupling involves the amide bond formation . Convert acid into acyl halide on treatment with thionyl chloride and the react the acyl halide with amine by stirring at room temperature to get desired product.

Hi what’s the in between step after the conversion to the acid chloride? Do you directly add the amine into the same pot? Do you use a base such as triethylamine ?