Dimethylformamide → HCID 59239434, compound

Participants

Reaction Steps

3-Chloropyrazine-2-carboxylic acid (0.0648 g, 0.000409 mol) in dry Methylene chloride (1.50 mL, 0.0234 mol) was added N,N-Dimethylformamide (0.00200 mL, 0.0000258 mol) followed by Oxalyl chloride (0.040 mL, 0.00047 mol) dropwise. The reaction mixture was stirred for 3 hours then concentrated, added 1-ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.102 g, 0.000267 mol), N,N-Dimethylformamide (1.80 mL, 0.0232 mol), and N,N-Diisopropylethylamine (0.180 mL, 0.00103 mol) and stirred overnight. The reaction mixture was filtered and purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.76 (dd, J=5.6, 2.5, 1H), 8.70-8.60 (m, 2H), 8.17 (dd, J=39.6, 8.8, 2H), 7.47 (dd, J=23.6, 8.8, 2H), 6.17 (dd, J=13.2, 5.7, 1H), 4.79 (s, 1H), 4.42 (s, 1H), 3.91 (t, J=5.4, 1H), 3.80-3.66 (m, 4H), 3.54-3.41 (m, 5H), 3.19-3.05 (m, 2H), 2.81 (t, J=5.1, 1H), 2.69 (t, J=5.0, 1H), 1.06 (q, J=7.2, 3H). LC/MS-m/z+523.2 (M+H)+.

Provenance & Evidence