Hydrochloric Acid → HCID 178424096, compound

Participants

Reaction Conditions

Reaction Steps

cis-Ethyl 4-(4-amino-3-{4-[(5,7-dimethyl-1,3-benzoxazol-2-yl)amino]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-cyclohexanecarboxylate (0.10 g, 0.19 mmol), aqueous sodium hydroxide (1 M, 2 mL, 2 mmol), and methanol (2 mL) were combined and heated under an air condenser at 70° C. for 14 h. The residue was acidified with aqueous hydrochloric acid (3 M, 2 mL, 6 mmol), and extracted with 10% methanol/dichloromethane (3×20 mL). The combined organic fractions were dried over magnesium sulfate, filtered, and concentrated. Purification of the product by preparative HPLC (25 to 100% acetonitrile in 0.1 M aqueous ammonium acetate over 20 min at 21 mL/min using an 8μ Hypersil HS C18, 250×21 mm column, Rt 8.8-10.9 min) afforded cis-4-(4-Amino-3-{4-[(5,7-dimethyl-1,3-benzoxazol-2-yl)amino]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-cyclohexanecarboxylic acid as a cream-colored powder (0.026 g, 0.052 mmol); RP-HPLC (25 to 100% acetonitrile in 0.1 M aqueous ammonium acetate over 10 min at 1 mL/min using a 5μ Hypersil HS C18, 250×4.6 mm column) Rt 9.03 min; MS (MH)+ 498.

Provenance & Evidence