Triethylamine → HCID 178495806, compound

Participants

Reaction Steps

The 2-chloroquinoline-4-carboxylic acid (TCI-JP, 0.29 g, 1.4 mmol) was converted to 2-chloroquinoline-4-carbonyl chloride with 5 mL of thionyl chloride using the method described in Example 134A. The product of Example 126A (0.20 g, 1.1 mmol), Et3N (0.3 mL, 2.2 mmol) and 2-chloroquinoline-4-carbonyl chloride in 30 mL THF were processed as in Example 134B to afford the title compound (0.14 g, 0.37 mmol, 35% yield). 1H NMR (300 MHz, CD3OD) δ ppm 2.33 (s, 3H), 2.35 (s, 3H), 3.31 (s, 3H), 3.78 (t, J=5.3 Hz, 2H), 4.49 (t, J=5.3 Hz, 2H), 7.66 (ddd, J=8.5, 7.1, 1.4 Hz, 1H), 7.81 (ddd, J=8.5, 7.1, 1.4 Hz, 1H), 7.94 (s, 1H), 7.99 (dt, J=8.5, 0.7 Hz, 1H), 8.83 (dd, J=8.6, 1.2 Hz, 1H); MS (DCI/NH3) m/z 376 (M+H)+; Anal. calculated for C18H18ClN3O2S: C, 57.52; H, 4.83; N, 11.18. Found: C, 57.44; H, 4.59; N, 10.97.

Provenance & Evidence