Sodium Hydroxide → HCID 67124533, compound

Participants

Reaction Conditions

Reaction Steps

To an EtOH solution (10 mL) of ethyl 6-cyclopropyl-3-methyl-1-(1-methyl-4-piperidinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (620 mg, 1.811 mmol) was added sodium hydroxide (5.43 mL, 5.43 mmol) and the mixture heated at 70° C. for 1 hour. The solvent was removed in vacuo and the residue was dissolved in 20 mL of water. The contents were acidifed with acetic acid, and extracted with EtOAc (4×30 mL). The combined organic extracts were washed with water, brine, dried over MgSO4, filtered, and concentrated in vacuo to afford a minor amount of product. The aqueous phase was concentrated in vacuo and the crude residue purified by reverse phase HPLC purification (eluent: 0% ACN/H2O, 0.1% TFA to 45% ACN/H2O, 0.1% TFA). The isolated solid product was concentrated from toluene to afford the final product as 510 mg (90%). LCMS E-S (M+H)=315.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.08 (d, J=6.57 Hz, 4 H), 2.10 (d, J=13.14 Hz, 2 H), 2.30-2.42 (m, 3 H), 2.55 (s, 3 H), 2.77-2.92 (m, 3 H), 3.30 (br. s., 2 H), 3.57 (d, J=12.13 Hz, 2 H), 4.98 (m, J=11.78, 11.78, 3.85, 3.66 Hz, 1 H), 7.46 (s, 1 H), 9.87 (br. s., 1 H).

Provenance & Evidence