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

HRID 31476

反応式

HRID 31476 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-365a2c87d9bb4f109812fcc566843ee4
出典データセット
uspto-grants-2008_09
特許番号
US07425555B2

関連ノート

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