Triethylamine → HCID 54692287, compound

Participants

Reaction Steps

To a solution of 2-(4-Fluorobenzyl)-9-hydroxy-7-(morpholin-3-ylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione mono TFA salt (50 mg, 0.096 mmol, from Example 17) in DMF (1 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (28 mg, 0.145 mmol), 1-hydroxybenzotriazole hydrate (22 mg, 0.145 mmol), triethylamine (30 μL, 0.212 mmol), and (dimethylamino)(oxo)acetic acid (22 mg, 0.12 mmol). The reaction was stirred overnight at room temperature and equal amount of the reagents were added to the flask in the morning. After two hours the reaction was purified by prep HPLC on a C18 stationary phase with a water/acetonitrile/TFA gradient. The title compound as obtained as a white solid after lyophilization from dioxane. 1H NMR (400 MHz, d6 DMSO) Mixture of rotamers, approximately 1:1. δ 11.8 (2bs, 1H), 7.40 (m, 2H), 7.21 (m, 2H), 4.61-4.77 (m, 4H), 4.05 (m, 0.5H), 3.78-3.99 (m, 5H), 3.67 (m, 0.5H), 3.55-3.61 (m, 3H), 3.31-3.43 (m, 1.5H), 3.08 (m, 0.5H), 2.84, 2.81 (2s, 3H), and 2.76, 2.75 (2s, 3H). HRMS (FT-ICR) C23H26FN5O7+H=504.1873; calculated 504.1889.

Provenance & Evidence