Sodium Hydroxide → HCID 59267463, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 5-({6-chloro-5-[4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl]-1H-benzimidazol-2-yl}oxy)-2-methylbenzoate (43 mg, 0.086 mmol) was dissolved in MeOH (1.7 mL). Then 2.5 M aqueous NaOH (0.5 mL, 1.250 mmol) was added, and the reaction was stirred at 50° C. for 2 h. The reaction mixture was concentrated, and then partitioned between EtOAc and water. The aqueous phase was acidified to pH=1 with 2 N aqueous HCl and extracted with EtOAc. The combined organic extracts were dried (MgSO4), filtered and concentrated to give the desired product as an off-white solid. LC-MS: calculated for C27H20ClN3O4 485.11, observed m/e 486.25 (M+H)+ (Rt: 1.85 min). 1H NMR (500 MHz, C2D6OS): δ 8.20 (s, 1H), 7.90 (d, 1H), 7.80 (s, 1H), 7.65 (d, 2H), 7.55 (s, 1H), 7.45-7.50 (m, 3H), 7.41 (d, 1H), 7.35 (s, 1H), 6.5 (d, 1H), 3.5 (s, 3H). 2.55 (s, 3H).

Provenance & Evidence