3-Pyridinemethanamine → HCID 11614063, compound

Participants

Reaction Steps

The above carboxylic acid (75 mg, 0.15 mmol), 3-(aminomethyl)pyridine (25 mg, 0.23 mmol) and HATU (85 mg, 0.23 mmol) were dissolved in DMF (1.5 mL). N,N-Diisopropylethylamine (78 μL, 0.45 mmol) was added and the reaction was stirred overnight. Water was added and the resulting solution was extracted with CH2Cl2 (4×30 mL). The combined organic extracts were washed with 5% LiCl solution, dried over MgSO4, filtered, and concentrated. The residue was purified by semi-prep HPLC. The product fractions were concentrated and sodium bicarbonate added. The resulting solid was collected by vacuum filtration, washed with water, and dried under vacuum at 55° C. to provide the title compound (48 mg, 54%) as white solid: mp 127-133° C.; ESI MS m/z 591 [C30H34N6O5S+H]+; HPLC>95%, tR=15.03 min.

Provenance & Evidence