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Benzoyl chloride → 4'-{5-[(Benzoylamino)methyl]-1,3,4-oxadiazol-2-yl}-N-cyclopropyl-6-methyl-1,1'-biphenyl-3-carboxamide

HRID 31476
Notes
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Reaction equation

HRID 31476 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][CH2:11][C:12]1[O:16][C:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[C:28]([CH3:29])=[CH:27][CH:26]=[C:25]([C:30]([NH:32][CH:33]4[CH2:35][CH2:34]4)=[O:31])[CH:24]=3)=[CH:19][CH:18]=2)=[N:14][N:13]=1.C(N(CC)CC)C>C1COCC1>[C:1]([NH:10][CH2:11][C:12]1[O:16][C:15]([C:17]2[CH:18]=[CH:19][C:20]([C:23]3[C:28]([CH3:29])=[CH:27][CH:26]=[C:25]([C:30]([NH:32][CH:33]4[CH2:35][CH2:34]4)=[O:31])[CH:24]=3)=[CH:21][CH:22]=2)=[N:14][N:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 99978914'-[5-(aminomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1'-biphenyl-3-carboxamide

Product 1

HCID 104790204'-{5-[(Benzoylamino)methyl]-1,3,4-oxadiazol-2-yl}-N-cyclopropyl-6-methyl-1,1'-biphenyl-3-carboxamide

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

A solution of benzoyl chloride (6.3 μl) in THF (1 ml) was added dropwise to 4′-[5-(aminomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide (Example 53) (18.8 mg) and triethylamine (7.5 μl) in THF (4 ml). The reaction was stirred at room temperature for 16 hours, the solvent evaporated, the residue dissolved in water (10 ml) and extracted with DCM (2×10 ml). The combined organics were reduced to dryness under vacuum, the residue dissolved in methanol and the solution applied to a bond-elut (aminopropyl, 1 g), eluting with further methanol. The eluent was reduced to ca 10 ml in vacuo and passed through a bond-elut (SCX, 2 g), eluting with methanol. The solvent was evaporated from the eluent under vacuum. The residue was applied to a bond-elut (silica, 2 g) and eluted with an ethyl acetate/cyclohexane gradient to give, after evaporation of the solvent 4′-{5-[(benzoylamino)methyl]-1,3,4-oxadiazol-2-yl}-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide.

Workup

  1. customthe solvent evaporated
  2. dissolutionthe residue dissolved in water (10 ml)
  3. extractionextracted with DCM (2×10 ml)
  4. dissolutionthe residue dissolved in methanol
  5. washeluting with further methanol
  6. washeluting with methanol
  7. customThe solvent was evaporated from the eluent under vacuum
  8. washeluted with an ethyl acetate/cyclohexane gradient
  9. customto give
  10. customafter evaporation of the solvent 4′-{5-[(benzoylamino)methyl]-1,3,4-oxadiazol-2-yl}-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide

Sources & evidence

ORD record
ord-365a2c87d9bb4f109812fcc566843ee4
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07425555B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes