8-Quinolinecarboxylic acid → HCID 58711932, compound

Participants

Reaction Steps

In a similar manner as described for Intermediate 18, 6-(1-aminoethyl)-N-(3,4,5-trimethoxyphenyl)-1,2,4-triazin-3-amine (Intermediate 9) (0.123 g, 0.40 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.152 g, 0.40 mmol), quinoline-8-carboxylic acid (0.070 g, 0.40 mmol), diisopropylethylamine (0.14 mL, 0.80 mmol) in DMF (2 mL) gave N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)quinoline-8-carboxamide (0.180 g) as an orange solid. 1H NMR (CDCl3): δ8.95 (dd, J=4.4, 1.8 Hz, 1H), 8.83 (dd, J=7.4, 1.6 Hz, 1H), 8.50 (s, 1H), 8.30 (dd, J=8.2, 1.8 Hz, 1H), 7.99 (dd, J=8.3, 1.6 Hz, 1H), 7.71-7.65 (m, 1H), 7.53-7.48 (m, 1H), 7.42 (bs, 1H), 6.95 (s, 2H), 5.60 (p, J=7.1 Hz, 1H), 3.88 (s, 6H), 3.82 (s, 3H), 1.87 (d, J=7.1 Hz, 3H). MS m/z 461 (M+1).

Provenance & Evidence