Sodium ethoxide → N-Cyclopropyl-4'-[5-(ethoxymethyl)-1,3,4-oxadiazol-2-yl]-6-methyl-1,1'-biphenyl-3-carboxamide

HRID 31492Notes

Reaction equation

HRID 31492 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.[O-:27][CH2:28][CH3:29].[Na+]>>[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][O:27][CH2:28][CH3:29])=[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

3

Reactant 2

HCID 2723922Sodium ethoxideHCID 693148754'-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1'-biphenyl-3-carboxamide2×

Product 1

HCID 10452208N-Cyclopropyl-4'-[5-(ethoxymethyl)-1,3,4-oxadiazol-2-yl]-6-methyl-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) (50 mg) was added to a freshly prepared sodium ethoxide solution (0.087M, 2 ml), and the reaction stirred at room temperature for 72 hours. The reaction was partitioned between ethyl acetate and water, the organic phase dried (sodium sulphate) and reduced to dryness under vacuum. The residue was purified by HPLC to give, after evaporation of the solvent, N-cyclopropyl-4′-[5-(ethoxymethyl)-1,3,4-oxadiazol-2-yl]-6-methyl-1,1′-biphenyl-3-carboxamide.

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. dry with materialthe organic phase dried (sodium sulphate)
  3. customThe residue was purified by HPLC
  4. customto give
  5. customafter evaporation of the solvent, N-cyclopropyl-4′-[5-(ethoxymethyl)-1,3,4-oxadiazol-2-yl]-6-methyl-1,1′-biphenyl-3-carboxamide

Sources & evidence

ORD record
ord-f846bea5a2494fbd96c4f9ac70060235
Source dataset
uspto-grants-2008_09
Patent number
US07425555B2

Reaction notes

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