N,N'-Dimethylethylenediamine → HCID 22348000, compound

Participants

Reaction Steps

A solution of 8-Bromo-6-chloro-4-[1-benzo[1,3]dioxol-5-ylmethyl-piperidin-4-ylamino]chromen-2-one (30 mg, 0.061 mmol) in 0.3 mL toluene under nitrogen was treated with K2CO3 (20 mg, 0.13 mmol), about 3 mg CuI (0.016 mmol), 2-pyrrolidinone (10 uL, 0.13 mmol), followed by N,N′-dimethylethylenediamine (3 uL, 0.025 mmol) and heated to reflux. After 16 hours, the reaction was allowed to cool to room temperature, diluted with CH2Cl2, washed with distilled water, dried (Na2SO4) and concentrated. Purification by reverse phase HPLC (Zorbax C18, 21.2×250 mm column, 15 mL/min, 0 to 60% acetonitrile:water with 0.1% trifluoroacetic acid) followed by extraction into CH2Cl2 after basification with 1 M K2CO3, dried (Na2SO4) and concentrated to give the title compound (6 mg, 20%). 1H NMR (300 MHz, ppm, DMSO-d6) δ 1.6 (m, 2H), 1.8 (m, 2H), 2.1 (m, 4H), 2.7 (m, 2H), 3.4-3.5 (m, 3H), 3.72 (t, J=7 Hz, 2H) 5.23 (s, 1H), 5.92 (s, 2H), 6.68-6.80 (m, 3H), 7.27 (m, 1H), 7.62 (d, J=2.3 Hz, 1H), 8.20 (d, J=2.4 Hz, 1H). MS(ESI) 496 (M+H), 494 (M−H).

Provenance & Evidence