Ethyl 4'-(3-aminopropyl)-1,1'-biphenyl-4-carboxylate → ethyl 4'-[3-[[(2R)-2-(6-chloro-3-pyridyl)-2-hydroxyethyl]amino]propyl]-1,1'-biphenyl-4-carboxylate

HRID 1823104Notes

Reaction equation

HRID 1823104 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C@@H:29]2[CH2:31][O:30]2)=[CH:25][N:24]=1>C(O)C>[Cl:22][C:23]1[N:24]=[CH:25][C:26]([C@@H:29]([OH:30])[CH2:31][NH:1][CH2:2][CH2:3][CH2:4][C:5]2[CH:10]=[CH:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=3)=[CH:7][CH:6]=2)=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 22171365Ethyl 4'-(3-aminopropyl)-1,1'-biphenyl-4-carboxylateHCID 545744082-Chloro-5-[(2R)-oxiran-2-yl]pyridine

Product 1

HCID 86590692ethyl 4'-[3-[[(2R)-2-(6-chloro-3-pyridyl)-2-hydroxyethyl]amino]propyl]-1,1'-biphenyl-4-carboxylateYield 47.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 4′-(3-aminopropyl)-1,1′-biphenyl-4-carboxylate (200 mg), and 2-chloro-5-[(2R)-2-oxiranyl]-pyridine (71.5 mg) in ethanol (10 ml) was refluxed for 18 hours. The mixture was evaporated in vacuo. The residue was purified by column chromatography on silica gel (chloroform:methanol=100:1) to give ethyl 4′-[3-[[(2R)-2-(6-chloro-3-pyridyl)-2-hydroxyethyl]amino]propyl]-1,1′-biphenyl-4-carboxylate (96 mg) as a colorless foam.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-a4bb471b23dd4241af79560b8fbb4e6d
Source dataset
uspto-grants-2006_05
Patent number
US07037938B2

Reaction notes

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