Hydrochloric Acid → HCID 178467193, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of (2S,4R)-1-[2-(3-acetyl-6-cyano-indol-1-yl)-acetyl]-4-fluoro-pyrrolidine-2-carboxylic acid 3-chloro-2-fluoro-benzylamide (prepared as described in Example 616 (45.0 mg, 0.09 mmol) in water (2 mL) and isopropanol (1 mL) at RT were added sodium azide (24.0 mg, 0.360 mmol) and zinc bromide (40.0 mg, 0.180 mmol). The mixture was heated to 130° C. for 10 h in a microwave apparatus (Personnal Chemistry, Biotage). After cooling to RT, a 6N HCl solution was added to the mixture, followed by extraction with EtOAc (3×). The combined organics were washed with brine, dried (phase separator) and concentrated in vacuo. Purification of the residue by preparative HPLC (Waters Sunfire, C18-ODB, 5 μm, 30×100 mm, eluent: 20-100% CH3CN/H2O/20 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 40 mL/min) afforded after lyophilization the title compound as solid. MS (LC/MS): 542.0 [M+H]+; tR (HPLC conditions k): 3.15 min.

Provenance & Evidence