Hydrochloric Acid → HCID 178457749, compound

Participants

Reaction Conditions

Reaction Steps

0.19 g (0.32 mmol) of tert-butyl 5-(1-methyl-1-phenylethylcarbamoyl)-3-(4-morpholin-4-ylbenzoylamino)-1H-pyrazolo[4,3-d]thiazole-1-carboxylate dissolved in 7 ml of ethanol is placed in a 50 ml round-bottomed flask. 1.6 ml (6.4 mmol) of a 4M solution of hydrochloric acid in dioxane are then added and the reaction mixture is stirred for 15 hours at 25° C. A further 1.6 ml (6.4 mmol) of a 4M solution of hydrochloric acid in dioxane are then added and the mixture is stirred for 15 hours at 25° C. The reaction medium is then concentrated to dryness under reduced pressure (40° C.) and the residue is taken up in 40 ml of dichloromethane and 40 ml of water, and basified with 0.1N sodium hydroxide solution. The emulsion obtained is resorbed by saturation with sodium chloride. After separation of the phases by settling, the organic phase is dried over magnesium sulfate and concentrated to dryness under reduced pressure (40° C.). The yellow residue is purified by flash chromatography (msilica=30 g; eluent: 97/3 dichloromethane/methanol). 0.097 g of N-(1-methyl-1-phenylethyl)-3-(4-morpholin-4-ylbenzoylamino)-1H-pyrazolo[4,3-d]thiazole-5-carboxamide is thus obtained in the form of a yellow foam. m.p.K=266° C. 1H NMR (400 MHz, DMSO-d6): δ ppm 1.70 (s, 6H); 3.29 (masked m, 4H); 3.75 (m, 4H); 7.04 (d, J=8.5 Hz, 2H); 7.20 (t, J=7.5 Hz, 1H); 7.31 (t, J=7.5 Hz, 2H); 7.41 (d, J=7.5 Hz, 2H); 7.99 (d, J=8.5 Hz, 2H); 8.50 (broad s, 1H); 10.8 (broad m, 1H); 13.6 (broad m, 1H).

Provenance & Evidence