Hydrochloric Acid → HCID 21093943, compound

Participants

Reaction Conditions

Reaction Steps

A solution of NaNO2 (34 mg, 498 μmol) in H2O (0.8 mL) was added to a solution of 2-(3-amino-4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)-N-thiazol-2-ylpropionamide (EXAMPLE 171, 200 mg, 488 μmol) in 6M HCl (1.6 mL) at 0° C. The reaction was stirred at 0° C. for 35 min, before being added slowly to a stirred mixture of Cu powder (80 mg, 1.26 mmol) and 12M HCl (0.8 mL) at 0° C. The temperature was increased to 20° C., then stirring was continued for 1 h. The mixture was then heated at 60° C. for 1 h, before being cooled down to 20° C. and extracted with CH2Cl2 (3×15 mL). The organic extracts were dried (MgSO4), filtered, and concentrated to give a residue that was purified by RP-HPLC to furnish the title compound: RTA=3.17 min; m/z (ES+)=429.2 [M+H]+.

Provenance & Evidence