Sodium Hydroxide → HCID 57671621, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(6-(3,6-dihydro-2 H-pyran-4-yl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamido)acetic acid (71 mg, 198 μmol, Example 260)) and 1 N sodium hydroxide (988 μl, 988 μmol) in MeOH (5 mL) was treated with 10% Pd/C (5.3 mg, 49 μmol) under nitrogen atmosphere. The reaction vessel was degassed and backfilled with hydrogen (3×), and the mixture was stirred at 23° C. for 75 minutes under hydrogen atmosphere. The reaction mixture was filtered from the catalyst through a pad of Celite®, and the filter cake was washed with MeOH (50 mL). The combined filtrate was concentrated and acidified with concentrated HCl. The precipitated solid was collected by filtration, washed with water (10 mL), and dried in vacuo to give the title compound as a white solid. MS (ESI, pos. ion) m/z: 362 (M+1). 1NMR (400 MHz, DMSO-d6) δ ppm: 10.49 (s, 1 H), 8.80 (d, J=2.0 Hz, 1 H), 8.26 (d, J=1.8 Hz, 1 H), 4.14 (d, J=5.3 Hz, 1 H), 3.98 (d, J=10.4 Hz, 2 H), 3.69 (s, 3 H), 3.42-3.52 (m, 2 H), 2.91-3.09 (m, 1 H), 1.65-1.88 (m, 4H).

Provenance & Evidence