HCID 67272288, compound → HCID 11853942, compound

Participants

Reaction Steps

A solution of 2-t-butyl 3-ethyl 6-(3-t-butyl-5-(3-(3-(pyridin-3-yloxy)phenyl)ureido)-1H-pyrazol-1-yl)-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate (available from Example 179, 0.102 g, 0.160 mmol) in 3N HCl in MeOH (5 mL) was stirred for 1 h. The solvent was evaporated. The residue was dissolved in THF (2 mL). 2N NaOH was added (2 mL) and then MeOH until homogenous. The solution was stirred at RT for 1 h. The solvents were evaporated, the residue was purified by reverse phase chromatography followed by coevaporation with THF/HCl to yield 6-(3-t-butyl-5-(3-(3-(pyridin-3-yloxy)phenyl)ureido)-1H-pyrazol-1-yl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (20 mg, 100%) as a white solid. 1H NMR (400 MHz, CD3OD): δ 8.66 (d, J=2.8 Hz, 1H), 8.59 (d, J=5.2 Hz, 1H), 8.22 (ddd, J=9.2, 2.8, and 0.8 Hz, 1H), 8.05 (dd, J=8.8, 5.6 Hz, 1H), 7.58 (t, J=2.0 Hz, 1H), 7.54-7.46 (m, 3H), 7.42 (t, J=8.2 Hz, 1H), 7.21 (d, J=8.0 Hz, 1H), 6.89 (dd, J=8.4, and 2.4 Hz, 1H), 6.57 (s, 1H), 6.59 (d, J=16.0 Hz, 1H), 4.51 (d, J=16.0 Hz, 1H), 4.49 (dd, J=11.2, and 5.2 Hz, 1H), 3.60 (dd, J=18.0, and 4.8 Hz, 1H), 1.37 (s, 9H), acid, amine and urea protons not visible, one proton is buried under the MeOH peak; MS (EI) m/z: 527.2 (M+H+).

Provenance & Evidence