Sodium Hydroxide → HCID 68328053, compound

Participants

Reaction Steps

A mixture of 5-(3-(5-methoxypyridin-3-yl)-1-((4-methylphenyl)sulfonyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)-1,3,4-oxadiazol-2-amine (0.022 g, 0.048 mmol) and 1 M NaOH (aq.) (0.095 mL, 0.095 mmol) in 4 mL of EtOH was stirred overnight at RT. The reaction was then concentrated and the residue taken up in H2O and EtOAc. The EtOAc layer was put aside and the aqueous layer was acidified with 2 M HCl (aq.) and extracted with DCM and 3/1 CHCl3/i-PrOH (2×). The aqueous layer was concentrated to give an orange solid, which was washed with MeOH and the MeOH washes were dried over Na2SO4, filtered and concentrated to give an orange solid. The solid was triturated with DCM and the orange solid (20 mg) was collected by filtration. This material was purified by reverse phase HPLC (5-100% MeCN in H2O with 0.1% TFA) followed by silica gel chromatography (0-10% MeOH in DCM) to afford 5-(3-(5-methoxypyridin-3-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)-1,3,4-oxadiazol-2-amine (0.0022 g, 7.14 μmol, 15.00%) as a white solid. MS (ESI, pos. ion) m/z: 309.0 (M+1). 1H NMR (400 MHz, CD3OD) δ ppm 4.01 (3H, s), 7.92-7.99 (2H, m), 8.11 (1H, d, J=2.93 Hz), 8.23 (1H, s), 8.43-8.47 (1H, m), 9.03 (1H, d, J=1.76 Hz).

Provenance & Evidence