Hydrochloric Acid → HCID 19783205, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 39.5 mg (0.05 mmol) of ethyl 3-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-1-[2-chloro-5-(valerylamino)phenyl]-1H-pyrazole-5-carboxylate (from Example 1), 200 μL (0.5 mmol) of 2.5N NaOH, and 600 μL of methanol was stirred under N2 at 60° C. for 2 hours. The solution was cooled, diluted with 5 mL of H2O, and adjusted to approximately pH 2 by gradual addition of 2N HCl, resulting in precipitation. The precipitate was collected on a filter and dried to yield 37.8 mg (97%) of the title compound as a nearly white solid, mp>110° C. (gradual); homogeneous by TLC in 9:1 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 761 (M+1)+. 400 MHz 1H NMR (DMSO-d6) δ0.80 (t, J=7.3 Hz, 3H), 0.88, (t, J=7.3 Hz, 3H), 1.24, 1.31 (overlapping m, each 2H), 1.47 (m, 2H), 1.57 (m, 2H), 2.31 (t, J=7.4 Hz, 2H), 2.48 (t, 2H, partially obscured by DMSO peak), 4.18 (br, 2H), 7.09 (d, J=7.4 Hz, 1H), 7.21 (d, J=8.3 Hz, 2H), 7.27-7.74 (m, 10H), 7.87 (d, J=2.5 Hz, 1H), 8.17 (dd, J=8.0, 1.3 Hz, 1H).

Provenance & Evidence