Ethyl orthoformate → N-cyclopropyl-4'-(1,3,4-oxadiazol-2-yl)-6-methyl-1,1'-biphenyl-3-carboxamide

HRID 31475

Reaction equation

HRID 31475 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][NH2:23])=[O:21])=[CH:16][CH:15]=3)[C:10]([CH3:13])=[CH:11][CH:12]=2)=[O:6])[CH2:3][CH2:2]1.[CH2:24](OC(OCC)OCC)C>>[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[O:21][CH:24]=[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 2

HCID 31214Ethyl orthoformateHCID 11438287N-cyclopropyl-4'-(hydrazinocarbonyl)-6-methyl-1,1'-biphenyl-3-carboxamide2×

Product 1

HCID 10018845N-cyclopropyl-4'-(1,3,4-oxadiazol-2-yl)-6-methyl-1,1'-biphenyl-3-carboxamide

Procedure

N-Cyclopropyl-4′-(hydrazinocarbonyl)-6-methyl-1,1′-biphenyl-3-carboxamide (Intermediate 40) (50 mg) in triethylorthoformate (5 ml) was heated at 150° C. for 5 hours. The excess triethylorthoformate was evaporated under vacuum and the residue purified by bond-elut (silica), eluting with an ethyl acetate/cyclohexane gradient. The solvent was evaporated from the product fractions under vacuum to give N-cyclopropyl-4′-(1,3,4-oxadiazol-2-yl)-6-methyl-1,1′-biphenyl-3-carboxamide.

Workup

  1. customThe excess triethylorthoformate was evaporated under vacuum
  2. customthe residue purified by bond-elut (silica)
  3. washeluting with an ethyl acetate/cyclohexane gradient
  4. customThe solvent was evaporated from the product fractions under vacuum

Sources & evidence

ORD record
ord-22413f3ed106492bafad0f52a5d77a7c
Source dataset
uspto-grants-2008_09
Patent number
US07425555B2

Linked notes

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