Trifluoroacetic acid → HCID 178527587, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Example 275a (350 mg, crude, 0.414 mmol), cyclopropanesulfonyl chloride (116 mg, 0.828 mmol), and triethylamine (0.058 mL, 0.414 mmol) in THF (5 mL) was stirred at room temperature for 1 day and concentrated in vacuo. To the residue was added dioxane (5 mL) and NaOH (20%, 1 mL) and the mixture was heated at 85° C. for 1 hour. The reaction mixture was concentrated and purified by reverse-phase HPLC performed on a Phenomenex Luna C8 AXIA column (30×75 mm, 100 Å) using a gradient of 10% to 95% acetonitrile: 0.1% aqueous trifluoroacetic acid over 12 minutes at a flow rate of 50 mL/minutes to give the title compound (17 mg, 9.2% yield) as trifluoroacetic acid salts. MS (ESI) m/e 447 (M+H)+; 1H NMR (400 MHz, DMSO-d6) ppm 0.94 (d, J=6.41 Hz, 4H) 1.35-1.53 (m, 4H) 1.99-2.11 (m, 4H) 2.50-2.57 (m, 1H) 3.15-3.25 (m, 1H) 3.71-3.82 (m, 1H) 6.66-6.79 (m, 1H) 7.08 (s, 1H) 7.18 (dd, J=7.93, 4.58 Hz, 1H) 8.29 (dd, J=4.73, 1.68 Hz, 1H) 8.35 (s, 1H) 8.79 (d, J=7.02 Hz, 1H) 12.03 (s, 1H).

Provenance & Evidence