Tert-butyl 2-({5'-[(cyclopropylamino)carbonyl]-2'-methyl-1,1'-biphenyl-4-yl}carbonyl)hydrazinecarboxylate → N-cyclopropyl-4'-(hydrazinocarbonyl)-6-methyl-1,1'-biphenyl-3-carboxamide

HRID 31427

Reaction equation

HRID 31427 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:30])=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([NH:21][NH:22]C(OC(C)(C)C)=O)=[O:20])=[CH:15][CH:14]=3)[CH:12]=2)=[O:6])[CH2:3][CH2:2]1>Cl>[CH:1]1([NH:4][C:5]([C:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([NH:21][NH2:22])=[O:20])=[CH:15][CH:14]=3)[C:10]([CH3:30])=[CH:9][CH:8]=2)=[O:6])[CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 59263012Tert-butyl 2-({5'-[(cyclopropylamino)carbonyl]-2'-methyl-1,1'-biphenyl-4-yl}carbonyl)hydrazinecarboxylate2×

Product 1

HCID 11438287N-cyclopropyl-4'-(hydrazinocarbonyl)-6-methyl-1,1'-biphenyl-3-carboxamide

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of tert-butyl 2-({5′-[(cyclopropylamino)carbonyl]-2′-methyl-1,1′-biphenyl-4-yl}carbonyl)hydrazinecarboxylate (Intermediate 41) (2.37 g) in hydrogen chloride (4.0M solution in dioxane, 20 ml) was stirred at room temperature under nitrogen for 6 hours. The solvent was evaporated under vacuum, the residue was dissolved in water, basified with sodium hydroxide solution (2N) and extracted with ethyl acetate. The organic phase was dried (magnesium sulphate) and the solvent removed under vacuum to give the N-cyclopropyl-4′-(hydrazinocarbonyl)-6-methyl-1,1′-biphenyl-3-carboxamide.

Workup

  1. customThe solvent was evaporated under vacuum
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried (magnesium sulphate)
  5. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-abae4452f6fe457aab21c76e4e460e8b
Source dataset
uspto-grants-2008_09
Patent number
US07425555B2

Linked notes

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