Reacción #1135842

Ecuación de reacción

KOH

methyl 7-(1-cyclopropyl-1H-benzo[d]imidazol-2-yl)heptanoate

hydroxylamine

→

7-(1-cyclopropyl-1H-benzo[d]imidazol-2-yl)-N-hydroxyheptanamide

Rendimiento 63.9%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónbriefly concentrated
2. 2
   workup.ADDITIONby adding 1 N HCl solution until pH was 7
3. 3
   ExtracciónThe mixture was extracted with ethyl acetate
4. 4
   Otrodried
5. 5
   Concentraciónconcentrated
6. 6
   OtroThe residue was purified by biotage column chromatography

Procedimiento

To a solution of methyl 7-(1-cyclopropyl-1H-benzo[d]imidazol-2-yl)heptanoate (80 mg, 0.27 mmol) in THF at 0° C. was added 50% hydroxylamine solution (0.16 mL, 2.6 mmol). To this was added KOH (0.80 mL, 1M in MeOH, 0.80 mmol) dropwise. The reaction was stirred at 0° C. for 2 hr, briefly concentrated and neutralized by adding 1 N HCl solution until pH was 7. The mixture was extracted with ethyl acetate, dried and concentrated. The residue was purified by biotage column chromatography to give 7-(1-cyclopropyl-1H-benzo[d]imidazol-2-yl)-N-hydroxyheptanamide 24 (52 mg). MS (M+1=302)

Fuente