Reaction #59697

Reaction equation

tert-butyl 2-({5′-[(cyclopropylamino)carbonyl]-3′-fluoro-2′-methyl-1,1′-biphenyl-4-yl}carbonyl)hydrazinecarboxylate

Intermediate 30

tert-butyl 2-({5′-[(cyclopropylamino)carbonyl]-3′-fluoro-2′-methyl-1,1′-biphenyl-4-yl}carbonyl)hydrazinecarboxylate

Methanol

→

N-cyclopropyl-5-fluoro-4′-(hydrazinocarbonyl)-6-methyl-1,1′-biphenyl-3-carboxamide

Solvents

hydrogen chloride

Conditions

Workup

1. 1
   Otherto form a solution
2. 2
   Otherthe solvents evaporated under vacuum
3. 3
   workup.DISSOLUTIONThe residue was partially dissolved in water
4. 4
   Extractionextracted with ethyl acetate (120 ml)
5. 5
   OtherThe organic phase was dried
6. 6
   Otherthe solvent removed under vacuum

Procedure

A solution of tert-butyl 2-({5′-[(cyclopropylamino)carbonyl]-3′-fluoro-2′-methyl-1,1′-biphenyl-4-yl}carbonyl)hydrazinecarboxylate (Intermediate 30) (400 mg) in hydrogen chloride (4.0M solution in dioxane, 5 ml) was stirred at room temperature under nitrogen for 16 hours. Methanol was added to form a solution and the solvents evaporated under vacuum. The residue was partially dissolved in water, basified with sodium hydroxide solution (2N, 10 ml) and extracted with ethyl acetate (120 ml). The organic phase was dried and the solvent removed under vacuum to give the N-cyclopropyl-5-fluoro-4′-(hydrazinocarbonyl)-6-methyl-1,1′-biphenyl-3-carboxamide.

Source