Sodium hydride → HCID 53922765, compound

Participants

Reaction Conditions

Reaction Steps

To DMSO (3.5 mL) is added 60% NaH dipersion in mineral oil (84 mg, 2.1 mmol) and the resulting mixture stirred for 5 min. To this solution is added 4-(6-oxo-1,6-dihydro-pyridazin-3-yl)-benzoic acid methyl ester (460 mg, 2 mmol reference example 36e) and the mixture stirred for 10 min (till homogeneous). In a separate flask containing DMSO (3.5 mL) is added 60% NaH (101 mg, 2.5 mmol) and stirred 5 min. To this solution is added 2-dimethylaminoethylchloride hydrochloride (346 mg, 2.4 mmol) and let stir for 5 min. This solution is transferred to the reaction solution, heated to 50° C., let stir for 2 hours. Cooled to 20° C., quenched with sat NH4Cl soln (2 mL) and concentrated. The residue is purified by short path flash chromatography (eluting with 10% methanol in dichloromethane) to give 542 mg of title compound. 1H NMR (CD3OD) δ 2.35 (s, 6H), 2.88 (t, J=7 Hz, 2H), 3.93 (s, 3H), 4.42 (t, J=7 Hz, 2H), 7.08 (d, J=10 Hz, 1H), 8.06 (m, 5H). MS (EI) m/z 302 (M+H)+.

Provenance & Evidence