Methane → HCID 53791749, compound

Participants

Reaction Conditions

Reaction Steps

7-Chloroformyl-3-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole hydrochloride (12 g) is added, at a temperature between 60° and 70° C., to a solution of 2-amino-6-fluoropyridine (4.5 g) and triethylamine (8.1 g) in dioxane (250 cc) which is heated to a temperature in the vicinity of 60° C., in the course of 5 minutes. The suspension obtained is heated at a temperature in the vicinity of 100° C. for 6 hours and 45 minutes and then stirred at a temperature in the vicinity of 20° C. for 16 hours. The solvent is evaporated off under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 60° C. The residue obtained is dissolved in methylene chloride (500 cc) and the solution obtained is washed twice with distilled water (300 cc in total), twice with an aqueous 2N sodium hydroxide solution (300 cc in total) and twice with distilled water (300 cc in total) and then dried over anhydrous magnesium sulphate, treated with decolorizing charcoal (0.5 g), filtered and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 50 ° C. A crude product (11.4 g) is thereby obtained, which is dissolved in boiling butan-1-ol (70 cc). Decolorizing charcoal (0.5 g) is added to the solution obtained and the suspension is filtered in the heated state. The filtrate is cooled at a temperature in the vicinity of 4° C. for 2 hours. The crystals formed are separated by filtration, washed 3 times with butan-1-ol (45 cc in total), twice with ethanol (50 cc in total) and 3 times with diethyl ether (90 cc in total) and then dried under the reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 20° C. in the presence of potassium hydroxide pellets. N-(6-fluoro-2-pyridyl)-3-(3-pyridyl)-1H, 3H-pyrrolo[1,2- c]thiazole-7-carboxamide (5.3 g) in the form of beige-coloured crystals, m.p. 198° C., is thereby obtained.

Provenance & Evidence