Tetrabutylammonium Fluoride → HCID 45256867, compound

Participants

Reaction Conditions

Reaction Steps

TBAF (1M in THF) (0.35 mL, 0.35 mmol) was added to a solution of methyl 5-[(6-chloro-5-{4-[1-(hydroxymethyl)cyclopropyl]phenyl}-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate (275 mg, 0.464 mmol) in dioxane (5 mL) and reaction mixture was heated at 80° C. The volatiles were removed. The resulting crude residue was dissolved in MeOH (2 ml) and 2.5 N aqueous NaOH (2 mL) and stirred at 50° C. for 1 h. Volatiles were removed and the residue was partitioned between EtOAc and water. The aqueous layer was acidified to pH=1 with 2 N aqueous HCl, and extracted with EtOAc. Combined organic layers were dried (MgSO4), filtered and concentrated. Purification by reverse phase HPLC eluting with 10-100% acetonitrile:water afforded the title compound. LC-MS calculated for C25H21ClN2O4 448.12, observed m/e 448.7 (M+H)+. Rt: 1.81/4 min. 1H NMR (500 MHz, CD3OD): δ 7.85 (s, 1H), 7.50 (s, 1H), 7.40-7.45 (m, 4H), 7.35 (d, 2H), 7.30 (s, 1H), 3.65 (s, 2H), 2.61 (s, 3H), 0.85-0.95 (q, 4H).

Provenance & Evidence