Dichloromethane → HCID 5276323, compound

Participants

Reaction Conditions

Reaction Steps

N-(4-Chlorobenzyl)-2-(chloromethyl)-7-methyl-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide (Preparation 1, 100 mg) and diisopropylethylamine (0.13 mL) is added to a mixture of (S)-3-(phenylmethyl)morpholine (93 mg, prepared as described by Shawe, T. T. Syn. Comm. 1997,27,1777-1782) in DMF (5 mL). The mixture is heated at 90° C. for 3 hours. After cooling to room temperature, the solution is poured into CH2Cl2 (125 mL) and washed with water (2×100 mL). The organic layer is dried (Na2SO4) and the solution filtered. Evaporation of the solvent gives a residue which is purified by column chromatography (methanol/CH2Cl2, 0-6%) to obtain 80 mg of the title compound. Physical characteristics. 1H NMR (400 MHz, DMSO-d6) δ 10.61, 8.71, 7.41-7.20, 4.54, 4.20, 3.96, 3.91, 3.59, 3.41, 3.20, 2.89, 2.82-2.66, 2.40; MS (ESI+) m/z 522 (M+H).

Provenance & Evidence