Hydrochloric Acid → HCID 89525975, compound

Participants

Reaction Steps

To a flask containing (R)-tert-butyl 4-(2-(1-(6-(N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-5-chloro-2-oxobenzo[d]oxazol-3(2H)-yl)ethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (34-5) (16 mg, 0.026 mmol) (prepared by a sequence analogous to the synthesis of 16-4, vide supra) was added DCM (2 ml) & MeOH (2), then added saturated HCl in EtOAc (˜4N) (64.7 μl, 0.26 mmol). The reaction mixture was capped (not under N2) & stirred at room temperature. Followed by LC/MS. After 3 hours the reaction mixture was concentrated to yield (R)-5-chloro-2-oxo-3-(1-(2-(1,2,3,6-tetrahydropyridin-4-yl)phenyl)ethyl)-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide hydrochloride (34-6). HRMS [M+H] calculated; 518.0718, observed; 518.0706. 1H NMR (499 MHz, DMSO): δ 9.15 (d, J=33.1 Hz, 2H); 8.51 (s, 1H); 7.95 (s, 1H); 7.79 (d, J=7.7 Hz, 1H); 7.63-7.46 (m, 2H); 7.46-7.36 (m, 2H); 7.23 (s, 1H); 7.09 (d, J=7.3 Hz, 1H); 5.74-5.68 (m, 1H); 5.42 (br s, 1H); 3.65-3.54 (m, 1H); 3.35-3.23 (m, 1H); 3.18-3.09 (m, 2H); 2.67-2.55 (m 1H); 2.18-2.08 (m, 1H); 1.83 (d, J=7.1 Hz, 3H). Note: NMR peaks overlapping with solvent or water could not be accurately accounted for.

Provenance & Evidence