Ethyl Acetate → 5-(2-{[4-Chloro-3-(6-chloro-4-methyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-pentanoic acid methyl ester

HRID 1848589Notes

Reaction equation

HRID 1848589 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])[CH3:9])=[O:7])=[CH:4][C:3]=1[C:19]1[CH:20]=[N:21][C:22]([Cl:26])=[CH:23][C:24]=1[CH3:25].C[CH:28]([CH2:33][CH2:34][CH3:35])[C:29]([O:31]Br)=[O:30].[C:36]([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[CH3:36][O:31][C:29](=[O:30])[CH2:28][CH2:33][CH2:34][CH2:35][O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[N:8]([C:6](=[O:7])[C:5]1[CH:17]=[CH:18][C:2]([Cl:1])=[C:3]([C:19]2[CH:20]=[N:21][C:22]([Cl:26])=[CH:23][C:24]=2[CH3:25])[CH:4]=1)[CH3:9]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 866425714-chloro-3-(6-chloro-4-methyl-pyridin-3-yl)-N-(2-hydroxy-phenyl)-N-methyl-benzamideHCID 86642572Bromo methylvalerate

Product 1

HCID 593703575-(2-{[4-Chloro-3-(6-chloro-4-methyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-pentanoic acid methyl esterYield 35.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-chloro-3-(6-chloro-4-methyl-pyridin-3-yl)-N-(2-hydroxy-phenyl)-N-methyl-benzamide (108 mg, 0.28 mmol), bromo methylvalerate (60 μL, 0.42 mmol) and K2CO3 (116 mg, 0.84 mmol) in DMF (1 mL) was stirred at room temperature for 14 hrs. Ethyl acetate was added and the combined organic layers were washed with water, dried over MgSO4, then purified by silica gel column chromatography eluted with ethyl acetate/hexane (1/4) up to 1/3 to yield 5-(2-{[4-chloro-3-(6-chloro-4-methyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-pentanoic acid methyl ester 12-1 (50 mg). MS [M+H]+: 501; tR=8.52 min. (method 1)

Workup

  1. washthe combined organic layers were washed with water
  2. dry with materialdried over MgSO4
  3. custompurified by silica gel column chromatography
  4. washeluted with ethyl acetate/hexane (1/4) up to 1/3

Sources & evidence

ORD record
ord-3f5d71019b304ff985a76080540a4fed
Source dataset
uspto-grants-2015_02
Patent number
US08952161B2

Reaction notes

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