Nicotinic Acid → HCID 68982966, compound

Participants

Reaction Steps

A mixture of (1H-pyrrolo[2,3-c]pyridin-2-yl)methylamine dihydrochloride (Example 84) (110 mg, 0.50 mmol), nicotinic acid (62 mg, 0.50 mmol), diisopropylethylamine (0.44 mL, 2.5 mmol), EDCI (110 mg, 0.55 mmol) and HOBt (cat.) in methylene chloride (2.9 mL) and DMF (3 mL) was stirred at room temperature under a nitrogen atmosphere overnight (18 h). The reaction mixture was concentrated to dryness under reduced pressure. The residue was diluted with water. The water layer was concentrated to dryness. The residue was dissolved in ethanol (10 mL) and 2 N HCl in Et2O (10 mL) was added. Methanol (ca. 5 mL) was added to dissolve the majority of material. The remaining brown precipitate was filtered off and discarded. The filtrate was concentrated, and the resulting solid was triturated with EtOH (ca. 4 mL), filtered, and dried to provide N-(1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)nicotinamide dihydrochloride (31 mg, 19%) as a tan solid: 1H NMR (500 MHz, CD3OD) δ4.99 (2H, s), 7.00 (1H, s), 8.03 (1H, d, J=6.0 Hz), 8.17-8.24 (3H, m), 8.77 (1H, s), 9.04-9.12 (3H, m), 9.38 (1H, s); ESI MS m/z 253 [C14H12N4O+H]+; HPLC (Method A) >99% (AUC), tR=7.78 min.

Provenance & Evidence