Ethyl Acetate → 4-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-N-[2-(3-hydroxy-propoxy)-phenyl]-N-methyl-benzamide

HRID 661624Notes

Reaction equation

HRID 661624 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]([C:26]#[N:27])=[CH:23][C:24]=1[CH3:25].[C:28]([O-:31])([O-])=O.[K+].[K+].[C:34](OCC)(=O)[CH3:35]>CN(C=O)C>[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[O:16][CH2:34][CH2:35][CH2:28][OH:31])[CH3:9])=[O:7])=[CH:4][C:3]=1[C:19]1[CH:20]=[N:21][C:22]([C:26]#[N:27])=[CH:23][C:24]=1[CH3:25]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 686032284-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-N-(2-hydroxy-phenyl)-N-methyl-benzamide

Product 1

HCID 686027404-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-N-[2-(3-hydroxy-propoxy)-phenyl]-N-methyl-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-N-(2-hydroxy-phenyl)-N-methyl-benzamide 8-1 (50 mg, 0.13 mmol), 4-bromopropanol (18 μL, 0.2 mmol) and K2CO3 (55 mg, 0.40 mmol) in DMF (0.4 mL) was stirred at room temperature for 14 hrs. Ethyl acetate was added and the combined organic layers were washed with water, dried over Na2SO4, then purified by silica gel column chromatography eluting with ethyl acetate/hexane (2/3) up to 100% EtOAc to yield 4-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-N-[2-(3-hydroxy-propoxy)-phenyl]-N-methyl-benzamide (30 mg). Example 1. MS [M+H]+: 436.1; tR=2.19 min. (method 1)

Workup

  1. washthe combined organic layers were washed with water
  2. dry with materialdried over Na2SO4
  3. custompurified by silica gel column chromatography
  4. washeluting with ethyl acetate/hexane (2/3) up to 100% EtOAc

Sources & evidence

ORD record
ord-459e6fbdddf140b396671316e398fd3b
Source dataset
uspto-grants-2011_12
Patent number
US08084614B2

Reaction notes

Loading…