Hydrazine hydrate (1:1) → HCID 52936138, compound

Participants

Reaction Steps

To a solution of Intermediate 8 (420 mg, 0.9 mmol) in MeOH (40 mL) at 0° C. was added hydrazine monohydrate (0.22 mL, 4.6 mmol). After 15 min at 0° C., the reaction mixture was allowed to warm RT for 1 h and a further 2.5 equiv. of hydrazine hydrate before being heated to 40° C. for 15 min. The mixture was then concentrated to half volume and water was added. The aqueous layer was extracted with DCM (×2) and the organics were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was then dissolved in MeOH (30 mL) and trimethylorthoacetate (0.17 mL, 1.3 mmol) and PPTS (45 mg, 0.18 mmol) were added. The reaction mixture was refluxed for 45 min before being concentrated under reduced pressure. The crude mixture was dissolved in DCM and washed with water, dried over Na2SO4, filtered and concentrated in vacuo. The crude solid was then purified by flash chromatography on silica gel to give the title compound (70 mg, 16% yield over two steps) as a white solid. Rf=0.5 (DCM/MeOH:90/10). Mp >260° C. LC/HRMS (M+H)+ calculated for C26H2835ClN5O2 478.2010. Found 478.1968. Rt 2.76 min.

Provenance & Evidence