Reaction Steps
To a solution of 1-(4-(7-(benzyloxy)naphthalen-2-ylsulfonylcarbamoyl)-2-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-N,N-dibutyl-4-chloro-5-methyl-1H-pyrazole-3-carboxamide (Example 18, 30 mg, 0.035 mmol) in MeOH (5.0 mL) was added 10% Pd/C (75 mg, 0.71 mmol). The flask was evacuated and purged with H2 from a balloon (2×), and the reaction mixture was then stirred overnight under an atmosphere of H2. The reaction mixture was diluted with CH2Cl2 and filtered through a pad of CELITE®, washing with CH2Cl2. The filtrate was concentrated in vacuo and purified by preparative HPLC to give the title compound (12 mg, 43%). 1H NMR (1:1 CD3OD:CDCl3, 1:1 mixture of amide rotamers) δ 8.37 (s, 1H), 8.17-8.13 (m, 1H), 8.05 (s, 1H), 7.93 (s, 1H), 7.80-7.76 (m, 2H), 7.70 (d, J=8.9 Hz, 1H), 7.34 (dd, J=8.5, 1.3 Hz, 1H), 7.23 (s, 1H), 7.17-7.05 (m, 4.5H), 6.83 (d, J=7.9 Hz, 0.5H), 4.66 (br s, 2H), 4.41 (s, 1H), 3.88 (br s, 1H), 3.51 (br s, 2H), 3.04-3.00 (m, 1H), 2.81-2.78 (m, 1H), 2.24 (s, 1.5H), 2.20 (s, 1.5H), 1.49-1.42 (m, 1H), 1.40-1.33 (m, 2H), 1.30-1.16 (m, 5H), 1.09-0.96 (m, 2H), 0.90-0.84 (m, 3H), 0.72 (t, J=7.4 Hz, 1.5H), 0.67 (t, J=7.4 Hz, 1.5H); MS (ESI+) m/z 756.2 (M+H)+.
