Methyl iodide → HCID 178466940, compound

Participants

Reaction Steps

A suspension of N-[4-ethoxy-6-(4-oxo-2-thioxo-thiazolidin-5-ylidenemethyl)-quinolin-2-yl]-acetamide (example 6a, 50 mg, 0.11 mmol) in acetonitrile (1.5 ml) was reacted with diisopropylethyl amine (0.200 ml, 1.15 mmol) and methyl iodide (0.15 ml, 2.3 mmol) at rt for 30 min. The mixture was concentrated to dryness and the residue suspended in acetonitrile (1.5 ml). Diisopropylethyl amine (0.20 ml, 1.15 mmol) and 4-(2-aminoethyl)tetrahydropyran (0.075 ml, 0.58 mmol) were successively added at rt, and the mixture was stirred at rt overnight. The precipitate was collected by suction filtration, an washed with acetronitrile. It was then absorbed on SiO2 and purified on a silica gel column with a 0–10% methanol/ethyl acetate gradient to afford the product N-(4-ethoxy-6-{4-oxo-2[2-(tetrahydro-pyran-4-yl)-ethylamino]-4H-thiazol-5-ylidenemethyl}-quinolin-2-yl)-acetamide as a pale yellow solid (22 mg, 50%). LC-MS m/e 469 (MH+).

Provenance & Evidence