Potassium Iodide → N-Cyclopropyl-4'-{5[-(diethylamino)methyl]-1,3,4-oxadiazol-2-yl}-6-methyl-1,1'-biphenyl-3-carboxamide

HRID 31479

Reaction equation

HRID 31479 reaction equation
Cl[CH2:2][C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[C:16]([C:21]([NH:23][CH:24]4[CH2:26][CH2:25]4)=[O:22])[CH:15]=3)=[CH:10][CH:9]=2)=[N:5][N:4]=1.[I-].[K+]>C(NCC)C>[CH:24]1([NH:23][C:21]([C:16]2[CH:15]=[C:14]([C:11]3[CH:12]=[CH:13][C:8]([C:6]4[O:7][C:3]([CH2:2][N:23]([CH2:24][CH3:25])[CH2:21][CH3:16])=[N:4][N:5]=4)=[CH:9][CH:10]=3)[C:19]([CH3:20])=[CH:18][CH:17]=2)=[O:22])[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 4875Potassium IodideHCID 693148754'-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1'-biphenyl-3-carboxamide2×

Product 1

HCID 10408948N-Cyclopropyl-4'-{5[-(diethylamino)methyl]-1,3,4-oxadiazol-2-yl}-6-methyl-1,1'-biphenyl-3-carboxamide

Reagents, catalysts & solvents 1

HCID 8021DiethylamineSolvent

Procedure

4′-[5-(Chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide (Intermediate 45) (37 mg) and potassium iodide (5 mg) were mixed in diethylamine (3 ml) and the reaction stirred at room temperature for 18 hours. The excess amine was evaporated under vacuum and the residue purified by bond-elut (silica), eluting with an ethyl acetate/cyclohexane gradient. After evaporation of the solvent this gave N-cyclopropyl-4′-{5-[(diethylamino)methyl]-1,3,4-oxadiazol-2-yl}-6-methyl-1,1′-biphenyl-3-carboxamide.

Workup

  1. customThe excess amine was evaporated under vacuum
  2. customthe residue purified by bond-elut (silica)
  3. washeluting with an ethyl acetate/cyclohexane gradient
  4. customAfter evaporation of the solvent this gave N-cyclopropyl-4′-{5-[(diethylamino)methyl]-1,3,4-oxadiazol-2-yl}-6-methyl-1,1′-biphenyl-3-carboxamide

Sources & evidence

ORD record
ord-7660b4ebd735463abd0da9204de9da53
Source dataset
uspto-grants-2008_09
Patent number
US07425555B2

Linked notes

Loading…