L-Tartaric acid → HCID 67301025, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (1S)-1-[5-chloro-8-(3-fluorophenyl)cinnolin-7-yl]ethanamine (43 g, 140 mmol, 80-90% ee) in ethanol (640 mL) at 60° C. was treated with a solution of L-tartaric acid (20 g, 130 mmol) in ethanol (430 mL). The flask containing the acid was rinsed with ethanol (12 ml) and the rinse solution was added to the reaction mixture at 60° C. The reaction mixture was stirred at 60° C. for 15 minutes and at room temperature for 18 hours. The solid that precipitated was collected by filtration and rinsed with ice-cold ethanol (9 mL) followed by 2-methoxy-2-methylpropane (3×18 ml) to give the desired product (43 g, 73%) as an off-white solid with 99.4% ee. 1H NMR determined that the amine to acid ratio was 1:0.75. LCMS for the free amine C16H14ClFN3 (M+H)+: m/z=302.1; Found: 302.0; 1H NMR (400 MHz, DMSO-d6): δ 9.53 (d, J=6.0 Hz, 1H), 8.47 (d, J=0.6 Hz, 1H), 8.35 (d, J=6.0 Hz, 1H), 7.62-7.54 (m, 1H), 7.37-7.19 (m, 3H), 4.18-4.13 (m, 1H), 3.92 (s, 1.5H, tartaric acid), 1.38-1.34 (m, 3H).

Provenance & Evidence