Pyridine → HCID 131714823, compound

Participants

Reaction Steps

N-[[6-methoxy-5-(tridecafluorohexyl)-1-naphthalenyl]carbonyl-N-methylglycine, methyl ester (100 mg, 0.165 mmol), prepared as in Example 5, phosphorus pentasulfide (67 mg) and dry pyridine (2 ml) were refluxed for 2 hours. After stirring overnight at room temperature, the mixture was refluxed for 2 additional hours, poured into water and extracted with ether. The ether extract was washed with 1N aqueous hydrochloric acid, water, saturated sodium bicarbonate and brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated giving 92.8 mg of the crude N-[[6-methoxy-5-(tridecafluorohexyl)-1-naphthalenyl]thioxomethyl]-N-methylglycine, methyl ester, which was used in the next preparation without further purification. ms: m/e 622 (M+H)+, 562, 519, 503, 352. nmr (CDCl3): δ2.84 & 3.04 (2s, 3H, N--CH3, rotamers); δ3.82 & 3.95 (2s, 3H, O--CH3, rotamers) δ3.4 & 5.5 (2d, 2 H, CH2, J=17); δ7.3 (m, 3H, Har); δ8.2 (m, 2H, Har).

Provenance & Evidence