Ammonium formate → HCID 59060811, compound

Participants

Reaction Steps

4-((2R)-2-{[[(2S)-2-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}-3-(phenyloxy)propyl](phenylmethyl)amino]methyl}-3,4-dihydro-2H-chromen-6-yl)-2-pyridinecarboxamide (Example 89, 44 mg, 0.07 mmol) was added to a suspension of 10% Pd/C (44 mg) in methanol (3 mL). Ammonium formate (22 mg, 0.35 mmol, 5.0 eq.) was added, and the mixture was heated at reflux for 30 minutes. Solids were removed by filtration through Celite®, and the filtrate was concentrated in vacuo. The title compound was collected as a pale yellow oil (25 mg, 66%): 1H NMR (300 MHz, acetone-d6) δ8.58 (d, 1 H), 8.32 (d, 1 H), 7.96 (broad s, 1 H), 7.78 (dd, 1 H), 7.60-7.56 (m, 2 H), 7.30-7.24 (m, 2 H), 6.95-6.81 (m, 4 H), 6.80 (broad s, 1 H), 4.25-4.19 (m, 2 H), 4.15-4.07 (m, 1 H), 3.99-3.92 (m, 1 H), 2.99-2.86 (m, 6 H), 2.13-2.06 (m, 1 H), 1.90-1.80 (m, 1 H), 0.92 (s, 9 H), 0.16 (s, 3 H), 0.13 (s, 3 H); MS m/z 548.3 (MH+).

Provenance & Evidence