methyl [3-[2-[(E)-3-(3-pyridyl)acryloylamino]ethyl]phenoxy]acetate → (E)-N-[3-[(methyl-carbamoyl) methoxy]phenethyl]-3-(3-pyridyl)-2-propenoic acid amide

HRID 428136Notes

Reaction equation

HRID 428136 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](/[CH:7]=[CH:8]/[C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:15]=[C:16]([CH:23]=[CH:24][CH:25]=2)[O:17][CH2:18][C:19]([O:21]C)=O)=[O:10])[CH:2]=1.[CH3:26][NH2:27].CO>CO>[CH3:26][NH:27][C:19]([CH2:18][O:17][C:16]1[CH:15]=[C:14]([CH:25]=[CH:24][CH:23]=1)[CH2:13][CH2:12][NH:11][C:9](=[O:10])/[CH:8]=[CH:7]/[C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)=[O:21]

Participants

4

Reactant 2

HCID 20701346methyl [3-[2-[(E)-3-(3-pyridyl)acryloylamino]ethyl]phenoxy]acetateHCID 57454252Monomethylamine methanol

Product 1

HCID 20701410(E)-N-[3-[(methyl-carbamoyl) methoxy]phenethyl]-3-(3-pyridyl)-2-propenoic acid amideYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl [3-[2-[(E)-3-(3-pyridyl)acryloylamino]-ethyl]phenoxy]acetate (0.34 g, 1.0 mmol) obtained in Example 94 was dissolved in methanol (6 ml) and 40% methylamine-methanol solution (0.8 ml) was added and stirred at room temperature for 17 hours. After concentrating the reaction mixture under reduced pressure, the residue was recrystallized to yield the titled compound (0.30 g, 88%).

Workup

  1. concentrationAfter concentrating the reaction mixture under reduced pressure
  2. customthe residue was recrystallized

Sources & evidence

ORD record
ord-79678c02d7cc454e9768d133289dce14
Source dataset
uspto-grants-2001_11
Patent number
US06313153B1

Reaction notes

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