Sodium Hydroxide → HCID 11199788, compound

Participants

Reaction Conditions

Reaction Steps

The product of Step 1 (1.58 g, 5.70 mmol, 1 equiv) was dissolved in methanol (24 mL) and 2.5 N NaOH (8 mL) was added. The reaction was heated to 60° C. for 3 h. Upon cooling, the resulting mixture was partitioned between EtOAc and water. The aqueous layer was acidified to pH 1 and extracted with EtOAc. The phases were separated and the organic phase was concentrated in vacuo. The resulting residue (1.50 g, 5.70 mmol, 1.1 equiv) was dissolved in DMF (30 mL). 1H-indazol-5-amine (700 mg, 5.18 mmol, 1.0 equiv) and PS-carbodiimide resin (8.27 g, 7.77 mmol, 1.5 equiv) were added and the mixture stirred overnight at room temperature. The resin was removed by filtration and washed alternately with methanol and CH2Cl2, followed by diethyl ether. The filtrate was concentrated en vacuo to remove the volatile solvents. The residue was dissolved in EtOAc, washed twice with water and once with satd. NaHCO3. The organic phase was concentrated in vacuo and the residue was purified by reverse phase HPLC (Xterra Prep 19×50, 25 mL/min, 10-90% 5 mM aq. NH4HCO3/CH3CN over 9 minutes) to provide 8 mg (0.4%) of a white crystalline solid. MS (ES+) m/e 379 [M+H]+.

Provenance & Evidence