Ethylamine → HCID 11952360, compound

Participants

Reaction Steps

Aqueous ethylamine (70%, 0.35 mL, 4.4 mmol) was added to a stirred solution of chloride 112 (240 mg, 0.9 mmol) in DME (20 mL) and the solution stirred at reflux temperature for 4 h. The solvent was evaporated and the residue purified by chromatography, eluting with a gradient (0-10%) of MeOH/DCM, to give 1-oxide 113 (203 mg, 84%) as a yellow solid: mp (MeOH/EtOAc) 187-190° C.; 1H NMR δ 8.05 (s, 1H, H-9), 7.37 (s, 1H, H-5), 5.14 (br s, 1H, NH), 3.54 (dq, J=7.2, 1.3 Hz, 2H, CH2N), 3.06-3.21 (m, 3H, CH, CH2), 2.89-2.99 (m, 2H, CH2), 2.32 [s, 6H, N(CH3)2], 1.28 (t, J=7.2 Hz, 3H, CH3); 13C NMR δ 158.7, 152.1, 148.9, 140.9, 130.0, 120.8, 115.0, 67.7, 43.9 (2), 38.0, 37.1, 36.3, 14.8. Anal. calcd for C14H19N5O: C, 61.5; H, 7.0; N, 25.6. Found: C, 61.3; H, 7.1; N, 25.5%.

Provenance & Evidence