Reacción #48855

Ecuación de reacción

1-methyl-1H-pyrazol-3-amine

triethylamine

3-(benzyloxy)-5-[(1R)-2-methoxy-1-methylethoxy]benzoic acid

oxalyl chloride

→

desired compound

3-(Benzyloxy)-5-[(1R)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

Disolventes

DCM

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroorganics were removed in vacuo
2. 2
   workup.DISSOLUTIONThe crude material was dissolved in DCM (30 mL)
3. 3
   workup.STIRRINGThe mixture was stirred at ambient temperature for 24 hours
4. 4
   Otrothe organics evaporated in vacuo
5. 5
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (100 mL)
6. 6
   Lavadowashed with 1M aqueous hydrochloric acid (50 mL) and brine (50 mL)
7. 7
   Secadodried (MgSO4)
8. 8
   Filtraciónfiltered
9. 9
   Otroevaporated in vacuo
10. 10
    Otroto give the crude product which
11. 11
    Otrowas chromatographed on silica
12. 12
    Lavadoeluting with a 50% ethyl acetate in isohexane

Procedimiento

DMF (2 drops) was added to a solution of 3-(benzyloxy)-5-[(1R)-2-methoxy-1-methylethoxy]benzoic acid (3.79 g, 0.012 mol) and oxalyl chloride (1.25 mL, 0.015 mol) in DCM (60 mL) and stirred for 3 hours, following which the organics were removed in vacuo. The crude material was dissolved in DCM (30 mL) and slowly added, at 0° C., to a stirred suspension of 1-methyl-1H-pyrazol-3-amine (1.22 g, 0.013 mol) and triethylamine (3.5 mL, 0.025 mol) in DCM (30 mL). The mixture was stirred at ambient temperature for 24 hours and the organics evaporated in vacuo. The residue was dissolved in ethyl acetate (100 mL), washed with 1M aqueous hydrochloric acid (50 mL) and brine (50 mL), dried (MgSO4), filtered and evaporated in vacuo to give the crude product which was chromatographed on silica, eluting with a 50% ethyl acetate in isohexane, to give the desired compound. (4.23 g).

Fuente