Reaction #48834

Reaction equation

3-{4-[(Hydroxyamino)(imino)methyl]phenoxy}-5-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

trimethyl orthoformate

→

desired compound

3-[(1S)-2-Methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[4-(1,2,4-oxadiazol-3-yl)phenoxy]benzamide

Conditions

Workup

1. 1
   workup.ADDITION2 drops of borontrifluoroetherate added
2. 2
   OtherThe volatiles were removed under reduced pressure
3. 3
   Otherthe resulting oil chromatographed on silica
4. 4
   Washeluting with 0-100% ethyl acetate in iso-hexane

Procedure

3-{4-[(Hydroxyamino)(imino)methyl]phenoxy}-5-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide was taken up in trimethyl orthoformate (3 mL) and 2 drops of borontrifluoroetherate added. The resulting solution was heated to 55° C. in a CEM explorer microwave for 80 mins. The volatiles were removed under reduced pressure and the resulting oil chromatographed on silica, eluting with 0-100% ethyl acetate in iso-hexane, to give the desired compound as a white foam (295 mg)

Source