Hydrochloric Acid → HCID 49839565, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 4-(4-(2,6-dichlorobenzamido)pyridin-2-ylamino)benzoate (500 mg, 1.2 mmol) in THF (30 mL) was added 2 N LiOH solution (2 mL, 1.5 mmol) dropwise. The reaction mixture was then stirred at 60° C. overnight. After cooling to room temperature, the reaction mixture was adjusted to pH=3-4 using HCl (2N, 2 mL). The mixture was extracted with EtOAc (3×50 mL). The combined organic extracts were washed with brine, dried over MgSO4 and concenrated under reduced pressure. The residue was purified by silica gel column chromatography (MeOH/CH2Cl2: 1/10) to afford desired product (440 mg, yield: 94%). 1H NMR (400 MHz, DMSO) δ 12.36 (s, 1H), 11.01 (s, 1H), 9.55 (s, 1H), 8.14 (d, J=5.7, 1H), 7.90-7.73 (m, 5H), 7.67-7.43 (m, 5H), 6.91 (dd, J=5.7, 1.6, 1H). LCMS (ESI) m/z: 403.4 [M+H+].

Provenance & Evidence