Dimethylamine → HCID 20773300, compound

Participants

Reaction Steps

Oxalyl chloride (0.08 ml, 0.88 mmol) was added to a solution of (R)-[(2S,5R)-2-methyl-5-methyl-4-(4-carboxyphenylsulphonyl)-1-(3,3,3-trifluoro-2-hydroxy-2-methylpropionyl)piperazine] (320 mg, 0.73 mmol) (Example 4) in DCM (25 ml). The resultant mixture was stirred at ambient temperature for 4 hours, evaporated to dryness, the residue treated with 40% aqueous dimethylamine (0.82 ml, 7.3 mmol) and the resultant mixture was stirred at ambient temperature overnight. The mixture was treated with EtOAc (25 ml), washed with 1 M hydrochloric acid, saturated sodium hydrogen carbonate solution and brine, dried and evaporated. The residue was chromatographed on silica with 50% EtOAc in DCM as eluent to give a solid which was recrystallized from EtOAc/hexane to give the title compound as a solid (26 mg, 0.056 mmol). Mp: 86-87° C.; NMR: 0.95 (d, 3H), 1.25 (dd, 3H), 1.65 (s, 3H), 2.95 (s, 3H), 3.1 (s, 3H), 3.25 (dd, 1H), 3.5 (dd, 1H), 4.2 (m, 2H), 4.5 (s, 1H), 4.8 (s, 1H), 7.5 (d, 2H), 7.85 (d, 2H); m/z: 464.

Provenance & Evidence