HCID 11350559, compound → HCID 59857422, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 2-(2-(2-tert-butylphenoxy)pyridin-3-ylamino)-3H-benzo[d]imidazole-5-carboxylate (Example 14, 65 mg, 0.156 mmol), in dry THF (6 mL) was added to a cooled (0° C.) solution of LiAlH4 in THF (0.39 mL, 1.0 M solution). After 2 h, the reaction was allowed to warrn to rt and stirred for 24 h. The mixture was cooled to 0° C., the excess of LiAlH4 was destroyed very with a saturated solution of NH4Cl. The product was extracted with EtOAc (4×20 mL), dried over MgSO4 and evaporated to yield a white solid. Example 145 was obtained after preparative HPLC purification (continuous gradient from 10% B to 60% B; A=90:10:0.1 H2O:MeOH:TFA; B=90:10:0.1 MeOH:H2O:TFA). tR=4.589 min (Shimadzu Phenomenex S5 ODS 4.6×50 mm Luna 4.6×50 mm; flow rate 2.5 mL/mn; detection at 220 nM; Gradient elution 0% to 100% B over 8 min; (A=10% MeOH, 90% H2O, 0.2% H3PO4 & B=90% MeOH, 10% H2O, 0.2% H3PO4). HRMS (ESI) m/z calcd for C23H25N4O2 [M+H]+389.1978, found 389.1972.

Provenance & Evidence