N,N-Dimethylethylenediamine → HCID 25140910, compound

Participants

Reaction Steps

N,N-Dimethyl-1,2-ethanediamine (0.40 mL, 3.6 mmol) was added to a stirred solution of chloride 196 (270 mg, 1.2 mmol) in DME (30 mL) and the solution stirred at reflux temperature for 4 h. The solvent was evaporated and the residue partitioned between DCM (100 mL) and dilute aqueous NH3 solution (50 mL). The organic fraction was dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (0-10%) of MeOH/DCM, to give 1-oxide 197 (216 mg, 65%) as a yellow solid: mp (MeOH/EtOAc) 153-157° C.; 1H NMR δ 7.50 (s, 1H, H-9), 7.40 (t, J=1.4 Hz, 1H, H-5), 5.73 (br s, 1H, NH), 4.67 (t, J=8.3 Hz, 2H, H-7), 3.48-3.53 (m, 2H, CH2N), 3.53 (dt, J=8.3, 1.4 Hz, 2H, H-6), 2.55 (dd, J=6.1, 5.9 Hz, 2H, CH2N), 2.28 [s, 6H, N(CH3)2]; 13C NMR δ 158.3, 158.2, 146.1, 140.6, 130.6, 121.8, 96.6, 71.9, 57.7, 45.1 (2), 38.8, 29.7. Anal. calcd for C13H17N5O2.¼CH3OH: C, 56.2; H, 6.4; N, 24.7. Found: C, 56.1; H, 6.2; N, 25.0%.

Provenance & Evidence