HCID 178465657, compound → HCID 178433934, compound

HRID 31495Notes

Reaction equation

HRID 31495 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[C:9]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([NH:22][NH:23][C:24](=[NH:26])[CH3:25])=O)=[CH:16][CH:15]=3)[C:10]([CH3:13])=[CH:11][CH:12]=2)=[O:6])[CH2:3][CH2:2]1>C1(C)C(C)=CC=CC=1>[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[C:9]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[NH:26][C:24]([CH3:25])=[N:23][N:22]=4)=[CH:16][CH:15]=3)[C:10]([CH3:13])=[CH:11][CH:12]=2)=[O:6])[CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 178465657HCID 178465657, compound2×

Product 1

HCID 178433934HCID 178433934, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

N-Cyclopropyl-4′-[(2-ethanimidoylhydrazino)carbonyl]-6-methyl-1,1′-biphenyl-3-carboxamide (intermediate 46) (80 mg) in xylene (15 ml) was heated at 190° C. under Dean-Stark conditions for 4 hours. The xylene was decanted from the precipitated solid and the solid washed with cyclohexane. The solid was applied to a bond-elut (silica) and eluted with an ethyl acetate/cyclohexane gradient to give, after evaporation of the solvents under vacuum, N-cyclopropyl-6-methyl-4′-(5-methyl-1,3,4-triazol-2-yl)-1,1′-biphenyl-3-carboxamide.

Workup

  1. customThe xylene was decanted from the precipitated solid
  2. washthe solid washed with cyclohexane
  3. washeluted with an ethyl acetate/cyclohexane gradient
  4. customto give
  5. customafter evaporation of the solvents under vacuum, N-cyclopropyl-6-methyl-4′-(5-methyl-1,3,4-triazol-2-yl)-1,1′-biphenyl-3-carboxamide

Sources & evidence

ORD record
ord-c345a41c374446919feab24e7e0b2825
Source dataset
uspto-grants-2008_09
Patent number
US07425555B2

Reaction notes

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