Sodium Methoxide → HCID 10317702, compound

HRID 31467

Reaction equation

HRID 31467 reaction equation
[CH3:1][O-:2].[Na+].Cl[CH2:5][C:6]1[O:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:22]([CH3:23])=[C:21]([F:24])[CH:20]=[C:19]([C:25]([NH:27][CH:28]4[CH2:30][CH2:29]4)=[O:26])[CH:18]=3)=[CH:13][CH:12]=2)=[N:8][N:7]=1>CO>[CH:28]1([NH:27][C:25]([C:19]2[CH:18]=[C:17]([C:14]3[CH:15]=[CH:16][C:11]([C:9]4[O:10][C:6]([CH2:5][O:2][CH3:1])=[N:7][N:8]=4)=[CH:12][CH:13]=3)[C:22]([CH3:23])=[C:21]([F:24])[CH:20]=2)=[O:26])[CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 10942334Sodium Methoxide2×HCID 693149174'-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-5-fluoro-6-methyl-1,1'-biphenyl-3-carboxamide2×

Product 1

HCID 10317702HCID 10317702, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

Freshly prepared sodium methoxide in methanol (0.2M, 0.8 ml) was added to a solution of (4′-[5-chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-5-fluoro-6-methyl-1,1′-biphenyl-3-carboxamide (Intermediate 34) (50 mg) in methanol (1 ml) and the reaction stirred at room temperature for 18 hours. Further sodium methoxide in methanol (0.2M, 1.6 ml) was added and the reaction continued for 72 hours. The reaction was reduced to dryness under vacuum and the residue partitioned between ethyl acetate and water. The organic phase was reduced to dryness and loaded onto a bond-elut (silica, 10 g). Eluted with an ethyl acetate/cyclohexane gradient. The solvent was evaporated from the product fractions under vacuum to give N-cyclopropyl-5-fluoro4′-[5-(methoxymethyl)-1,3,4-oxadiazol-2-yl]-6-methyl-1,1′-biphenyl-3-carboxamide.

Workup

  1. waitthe reaction continued for 72 hours
  2. customthe residue partitioned between ethyl acetate and water
  3. washEluted with an ethyl acetate/cyclohexane gradient
  4. customThe solvent was evaporated from the product fractions under vacuum

Sources & evidence

ORD record
ord-5a6be07d112d4df9a703a6ea1848b3aa
Source dataset
uspto-grants-2008_09
Patent number
US07425555B2

Linked notes

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