N,N-Dimethylethylenediamine → N1,N1-Dimethyl-N2-(1-oxido-7,8,9,10-tetrahydronaphtho[2,1-e][1,2,4]triazin-3-yl)-1,2-ethanediamine

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Reaction Steps

N,N-Dimethyl-1,2-ethanediamine (0.12 mL, 1.0 mmol) was added to a stirred solution of chloride 171 (83 mg, 0.4 mmol) in DME (20 mL) and the solution stirred at reflux temperature for 3 h. The solvent was evaporated and the residue partitioned between DCM (50 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 172 (84 mg, 84%) as a yellow solid: mp (MeOH) 151-153° C.; 1H NMR δ 7.31-7.36 (m, 2H, H-5, H-6), 5.75 (br s, 1H, NH), 3.51-3.55 (m, 2H, CH2N), 3.45-3.49 (m, 2H, CH2), 2.72-2.83 (m, 2H, CH2), 2.57 (br dd, J=6.0, 5.8 Hz, 2H, CH2N), 2.29 [s, 6H, N(CH3)2], 1.75-1.82 (m, 4H, 2×CH2); 13C NMR δ 158.4, 149.8, 137.4, 134.7, 132.4, 129.1, 123.5, 57.7, 45.0 (2), 38.6, 30.7, 29.3, 23.1, 21.6. Anal. calcd for C15H21N5O.½CH3OH: C, 61.4; H, 7.6; N, 23.1. Found: C, 61.2; H, 7.4; N, 23.4%.

Provenance & Evidence