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

HRID 31419Notes

Reaction equation

HRID 31419 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[C:9]([F:31])[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.CO>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])=[C:9]([F:31])[CH:8]=2)=[O:6])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 887MethanolHCID 69316615Tert-butyl 2-({5'-[(cyclopropylamino)carbonyl]-3'-fluoro-2'-methyl-1,1'-biphenyl-4-yl}carbonyl)hydrazinecarboxylate2×

Product 1

HCID 69318167N-cyclopropyl-5-fluoro-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]-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.

Workup

  1. customto form a solution
  2. customthe solvents evaporated under vacuum
  3. dissolutionThe residue was partially dissolved in water
  4. extractionextracted with ethyl acetate (120 ml)
  5. customThe organic phase was dried
  6. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-81ef2dbeee2d431589fa48b9340a6671
Source dataset
uspto-grants-2008_09
Patent number
US07425555B2

Reaction notes

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