2-Methoxyaniline → HCID 54596226, compound

Participants

Reaction Steps

CDI (92.98 mg, 0.5734 mmol) was added to a solution of 3-amino-6-anilino-pyrazine-2-carboxylic acid (110 mg, 0.4778 mmol) in DMF (1.5 mL) and the reaction stirred at ambient temperature for 1 hour. 2-Methoxyaniline (88.26 mg, 0.7167 mmol) was added and the reaction mixture left to stir at ambient temperature for 48 hours. The reaction mixture was purified directly by reverse phase preparative HPLC [Waters Sunfire C18, 10 mM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected, passed through a sodium bicarbonate cartridge and freeze-dried to give the title compound as an orange solid (14 mg, 9% Yield). 1H NMR (400.0 MHz, DMSO) δ 3.84 (s, 3H), 6.90-7.10 (m, 6H), 7.29-7.33 (m, 2H), 7.53-7.55 (m, 2H), 8.13 (s, 1H), 8.41-8.43 (m, 1H), 9.18 (s, 1H) and 10.15 (s, 1H) ppm; MS (ES+) 336.07.

Provenance & Evidence