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

HRID 31486

Reaction equation

HRID 31486 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+].[CH2:29]([NH2:31])[CH3:30]>C1COCC1>[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:31][CH2:29][CH3:30])=[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

5

Reactant 3

HCID 4875Potassium IodideHCID 6341EthylamineHCID 693148754'-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1'-biphenyl-3-carboxamide2×

Product 1

HCID 11740259N-Cyclopropyl-4'-{5-[(ethylamino)methyl]-1,3,4-oxadiazol-2-yl}-6-methyl-1,1'-biphenyl-3-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 ethylamine in THF (2M, 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-[(ethylamino)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-[(ethylamino)methyl]-1,3,4-oxadiazol-2-yl}-6-methyl-1,1′-biphenyl-3-carboxamide

Sources & evidence

ORD record
ord-867f7ea46b1e48a3b08a2fde80b2da55
Source dataset
uspto-grants-2008_09
Patent number
US07425555B2

Linked notes

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