Hydrochloric Acid → 3-[({[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic Acid

Participants

Reaction Steps

Methyl 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoate (3.02 g, 0.0064 mol) in MeOH (30 mL) was stirred with lithium hydroxide monohydrate (1.36 g, 0.032 mol) in H2O (15 mL) overnight at room temperature. The solution was treated with 3N HCl to adjust the pH to about 2.0 and cooled in an ice bath. Solid was collected and dried (2.4 g). The filtrate was treated with sat. aq. NaCl and extracted with EtOAc (2×). The extract was dried (Na2SO4) and concentrated to a residue. It was triturated with ether to afford the title compound as a white solid (143 mg only slightly inferior to the main product by LC-MS). Total product 2.56 g (88.7%). LC-MS m/z 452.1 (M+H)+.

Provenance & Evidence