Ethyl bromoacetate → Ethyl N-[2-{[2,2-bis(methyloxy)ethyl]amino}-6-(methyloxy)-3-pyridinyl]glycinate

HRID 657102Notes

Reaction equation

HRID 657102 reaction equation
[CH3:1][O:2][CH:3]([O:15][CH3:16])[CH2:4][NH:5][C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[C:8]([O:13][CH3:14])[N:7]=1.Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CN(C=O)C>[CH3:16][O:15][CH:3]([O:2][CH3:1])[CH2:4][NH:5][C:6]1[C:11]([NH:12][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:10][CH:9]=[C:8]([O:13][CH3:14])[N:7]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 86635355N2-[2,2-Bis(methyloxy)ethyl]-6-(methyloxy)-2,3-pyridinediamine

Product 1

HCID 68811995Ethyl N-[2-{[2,2-bis(methyloxy)ethyl]amino}-6-(methyloxy)-3-pyridinyl]glycinate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of N2-[2,2-bis(methyloxy)ethyl]-6-(methyloxy)-2,3-pyridinediamine (2.2 g, 10 mmol), ethyl bromoacetate (1.1 mL, 1.65 g, 10 mmol) and potassium carbonate (2.1 g, 20 mmol) in acetonitrile (50 mL) and DMF (5 mL) was stirred at room temperature overnight. The mixture was filtered and evaporated. The residue was dissolved in ethyl acetate and washed with water and brine. The organic extract was concentrated and added to a silica column which was then eluted with 0-100% ethyl acetate in hexane affording product (2.5 g, 82%).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water and brine
  5. extractionThe organic extract
  6. concentrationwas concentrated
  7. additionadded to a silica column which
  8. washwas then eluted with 0-100% ethyl acetate in hexane affording product (2.5 g, 82%)

Sources & evidence

ORD record
ord-c9089bf87fd34a388c34d7ae86ad33e5
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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