2-chloro-N-(2,4-dimethylphenyl)-N-isobutyl-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide → HCID 72191135, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-N-(2,4-dimethylphenyl)-N-isobutyl-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide (200 mg, 0.429 mmol) in N-methyl-2-pyrrolidone (NMP) (2 mL) was added copper(I) cyanide (77 mg, 0.858 mmol). The reaction vessel was sealed and heated by microwaves (Biotage Initiator) to 220° C. for 2 hours. After cooling the reaction LCMS analysis showed some evidence of the desired product. The reaction was reheated by microwaves to 220° C. for an additional 6 hours. The reaction was slowly and carefully quenched with dilute HCl (5 mL) and DCM (5 mL). The mixture was passed through a hydrophobic frit and the organic layer collected and concentrated in vacuo to give a brown oil. The crude was purified by mass directed autoprep (ammonium carbonate modifier). The appropriate fractions were evaporated in vacuo to give the required product, 56 mg. LCMS [LCMS2] Rt 1.47 min, m/z (ES+) 457 (M+H).

Provenance & Evidence