Pyridine → 3'-{({2-[4-(Aminosulfonyl)phenyl]ethyl}[(benzyloxy)acetyl]amino)methyl}-N-[2-(1-pyrrolidinyl)ethyl][1,1'-biphenyl]-3-carboxamide

HRID 9777

Reaction equation

HRID 9777 reaction equation
N1C=CC=CC=1.[CH2:7]([O:14][CH2:15][C:16](Cl)=[O:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH2:19][S:20]([C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][NH:31][CH2:32][C:33]2[CH:34]=[C:35]([C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([C:45]([NH:47][CH2:48][CH2:49][N:50]4[CH2:54][CH2:53][CH2:52][CH2:51]4)=[O:46])[CH:40]=3)[CH:36]=[CH:37][CH:38]=2)=[CH:25][CH:24]=1)(=[O:22])=[O:21]>CN(C=O)C.O>[NH2:19][S:20]([C:23]1[CH:24]=[CH:25][C:26]([CH2:29][CH2:30][N:31]([CH2:32][C:33]2[CH:34]=[C:35]([C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([C:45]([NH:47][CH2:48][CH2:49][N:50]4[CH2:54][CH2:53][CH2:52][CH2:51]4)=[O:46])[CH:40]=3)[CH:36]=[CH:37][CH:38]=2)[C:16](=[O:17])[CH2:15][O:14][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:27][CH:28]=1)(=[O:22])=[O:21]

Participants

6

Reactant 3

HCID 1049PyridineHCID 177085Benzyloxyacetyl chlorideHCID 102392483'-[{2-[4-(aminosulfonyl)phenyl]ethyl}aminomethyl]-N-[2-(1-pyrrolidinyl)ethyl][1,1'-biphenyl]-3-carboxamide

Product 1

HCID 102831223'-{({2-[4-(Aminosulfonyl)phenyl]ethyl}[(benzyloxy)acetyl]amino)methyl}-N-[2-(1-pyrrolidinyl)ethyl][1,1'-biphenyl]-3-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Pyridine (0.16 ml) and benzyloxyacetyl chloride (0.16 ml) were added to a solution of 3′-[{2-[4-(aminosulfonyl)phenyl]ethyl}aminomethyl]-N-[2-(1-pyrrolidinyl)ethyl]-[1,1′-biphenyl]-3-carboxamide (506 mg) in DMF (10 ml). The reaction mixture was stirred at room temperature for 16 hours, then diluted with water and extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residues were purified by silica gel column chromatography (dichloromethane/methanol=98/2), whereby the title compound (257 mg) was obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residues were purified by silica gel column chromatography (dichloromethane/methanol=98/2), whereby the title compound (257 mg)
  6. customwas obtained

Sources & evidence

ORD record
ord-d4cc21a4adb5481cb9c9581135c634cc
Source dataset
uspto-grants-2006_08
Patent number
US07091247B2

Linked notes

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