Ethyl bromoacetate → Ethyl N-[2-({2-[4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1-piperidinyl]ethyl}amino)-6-(methyloxy)-3-pyridinyl]glycinate

HRID 656961Notes

Reaction equation

HRID 656961 reaction equation
[NH2:1][C:2]1[C:3]([NH:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:15][CH2:14]2)=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CN(C=O)C>[CH3:24][C:22]([O:21][C:20]([NH:19][CH:16]1[CH2:15][CH2:14][N:13]([CH2:12][CH2:11][NH:10][C:3]2[C:2]([NH:1][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:7][CH:6]=[C:5]([O:8][CH3:9])[N:4]=2)[CH2:18][CH2:17]1)=[O:26])([CH3:23])[CH3:25]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 866353281,1-Dimethylethyl [1-(2-{[3-amino-6-(methyloxy)-2-pyridinyl]amino}ethyl)-4-piperidinyl]carbamate

Product 1

HCID 68810529Ethyl N-[2-({2-[4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1-piperidinyl]ethyl}amino)-6-(methyloxy)-3-pyridinyl]glycinate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 1,1-dimethylethyl [1-(2-{[3-amino-6-(methyloxy)-2-pyridinyl]amino}ethyl)-4-piperidinyl]carbamate (2.8 g, 7.6 mmol), ethyl bromoacetate (0.85 ml, 1.3 g, 7.6 mmol) and potassium carbonate (2 g, 15.2 mmol) in acetonitrile (40 ml) and DMF (20 ml) was stirred under argon overnight. The mixture was filtered, washing with acetonitrile, and evaporated. The residue was dissolved in the minimum volume of DCM (20 ml) and washed with water (20 ml). The organic extract was added to a silica column which was then eluted with 0-100% ethyl acetate in hexane affording a brown oil (1.3 g, 38%).

Workup

  1. filtrationThe mixture was filtered
  2. washwashing with acetonitrile
  3. customevaporated
  4. dissolutionThe residue was dissolved in the minimum volume of DCM (20 ml)
  5. washwashed with water (20 ml)
  6. extractionThe organic extract
  7. additionwas added to a silica column which
  8. washwas then eluted with 0-100% ethyl acetate in hexane affording a brown oil (1.3 g, 38%)

Sources & evidence

ORD record
ord-f799885e495f4c9bb702d4a8aca4dea2
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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