4'-[5-(azidomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1'-biphenyl-3-carboxamide → 4'-[5-(aminomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1'-biphenyl-3-carboxamide

HRID 31477

Reaction equation

HRID 31477 reaction equation
[N:1]([CH2:4][C:5]1[O:9][C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[C:21]([CH3:22])=[CH:20][CH:19]=[C:18]([C:23]([NH:25][CH:26]4[CH2:28][CH2:27]4)=[O:24])[CH:17]=3)=[CH:12][CH:11]=2)=[N:7][N:6]=1)=[N+]=[N-].[H][H]>[Pd].C(O)C>[NH2:1][CH2:4][C:5]1[O:9][C:8]([C:10]2[CH:11]=[CH:12][C:13]([C:16]3[C:21]([CH3:22])=[CH:20][CH:19]=[C:18]([C:23]([NH:25][CH:26]4[CH2:28][CH2:27]4)=[O:24])[CH:17]=3)=[CH:14][CH:15]=2)=[N:7][N:6]=1

Participants

5

Reactant 2

HCID 866046954'-[5-(azidomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1'-biphenyl-3-carboxamide2×HCID 178418361HCID 178418361, compound

Product 1

HCID 99978914'-[5-(aminomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1'-biphenyl-3-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4′-[5-(Azidomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide (Intermediate 44) (27.8 mg) and palladium on carbon (10% w/w, 5 mg) in ethanol (5 ml) were hydrogenated under 1 Atm. of hydrogen for 2 hours. The reaction was filtered through celite, the filtrate reduced to dryness under vacuum and the residue applied to a bond-elut (silica, 4 g). The column was eluted with chloroform, ether, ethyl acetate, and methanol. The methanol fraction was reduced to dryness under vacuum to give 4′-[5-(aminomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide.

Workup

  1. filtrationThe reaction was filtered through celite
  2. washThe column was eluted with chloroform, ether, ethyl acetate, and methanol

Sources & evidence

ORD record
ord-62f67bc2103c4ef5a310759ab4e930e7
Source dataset
uspto-grants-2008_09
Patent number
US07425555B2

Linked notes

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