Methyl 4'-[2-(benzylamino)ethyl]-1,1'-biphenyl-4-carboxylate → methyl 4'-[2-[N-benzyl-N-[(2R)-2-(6-chloro-3-pyridyl)-2-hydroxyethyl]amino]ethyl]-1,1'-biphenyl-4-carboxylate

HRID 1823127Notes

Reaction equation

HRID 1823127 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([C@@H:34]2[CH2:36][O:35]2)=[CH:30][N:29]=1>C(O)C>[CH2:1]([N:8]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[CH:19][C:20]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:22]=2)=[CH:13][CH:12]=1)[CH2:36][C@@H:34]([C:31]1[CH:30]=[N:29][C:28]([Cl:27])=[CH:33][CH:32]=1)[OH:35])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 22171573Methyl 4'-[2-(benzylamino)ethyl]-1,1'-biphenyl-4-carboxylateHCID 545744082-Chloro-5-[(2R)-oxiran-2-yl]pyridine

Product 1

HCID 86590696methyl 4'-[2-[N-benzyl-N-[(2R)-2-(6-chloro-3-pyridyl)-2-hydroxyethyl]amino]ethyl]-1,1'-biphenyl-4-carboxylateYield 70.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 4′-[2-(benzylamino)ethyl]-1,1′-biphenyl-4-carboxylate (460 mg), and 2-chloro-5-[(2R)-2-oxiranyl]pyridine (207 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 (chlorofor:methanol=100:1) to give methyl 4′-[2-[N-benzyl-N-[(2R)-2-(6-chloro-3-pyridyl)-2-hydroxyethyl]amino]ethyl]-1,1′-biphenyl-4-carboxylate (470 mg) as a colorless foam.

Workup

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

Sources & evidence

ORD record
ord-ad68d70f161d467e9adfe2f5fc23d793
Source dataset
uspto-grants-2006_05
Patent number
US07037938B2

Reaction notes

Loading…