Methylamine → HCID 22346269, compound

Participants

Reaction Steps

A suspension of 5-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide (12.0 g, 32 mmol) in DMSO (48 mL) was treated with methyl amine (48 mL of a 2M solution in THF, 96 mmol) and Hunig's base (11.1 mL, 86 mmol). The vessel was purged with argon, sealed and stirred at 135C for 3 days. The reaction was cooled, quenched with water (280 mL) and the pH adjusted to 5 by the addition of acetic acid. The reaction was stirred at room temperature for 1 hr and filtered. The solids were washed with water (100 mL) and then EtOAc (50 mL), and dried in vacuo to afford the title compound as a white solid.

Provenance & Evidence