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

HRID 31491

Reaction equation

HRID 31491 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+].[CH:29]1([CH2:32][NH2:33])[CH2:31][CH2:30]1>>[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][NH:33][CH2:32][CH:29]5[CH2:31][CH2:30]5)=[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 3

HCID 4875Potassium IodideHCID 75646CyclopropanemethanamineHCID 693148754'-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1'-biphenyl-3-carboxamide2×

Product 1

HCID 10408809N-Cyclopropyl-4'-(5-{[(cyclopropylmethyl)amino]methyl}-1,3,4-oxadiazol-2-yl)-6methyl-1,1'-biphenyl-3-carboxamide

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 cyclopropylmethylamine (3 ml) and the reaction stirred at room temperature for 18 hours. The excess amine was evaporated under vacuum and the residue purified by preparative HPLC. After evaporation of the solvent this gave N-cyclopropyl-4′-(5-{[(cyclopropylmethyl)amino]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 preparative HPLC
  3. customAfter evaporation of the solvent this gave N-cyclopropyl-4′-(5-{[(cyclopropylmethyl)amino]methyl}-1,3,4-oxadiazol-2-yl)-6-methyl-1,1′-biphenyl-3-carboxamide

Sources & evidence

ORD record
ord-3af7c8f51e0d4856adb4e19cfbfe30e7
Source dataset
uspto-grants-2008_09
Patent number
US07425555B2

Linked notes

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