Ethyl Acetate → tert-Butyl {1-[2-(6-methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)ethyl]piperidin-4-yl}carbamate

HRID 656962Notes

Reaction equation

HRID 656962 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][NH:17][C:18]2[C:23]([NH:24][CH2:25][C:26]([O:28]CC)=O)=[CH:22][CH:21]=[C:20]([O:31][CH3:32])[N:19]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])[CH3:3].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC.[O-2].[O-2].[Mn+4]>[CH3:32][O:31][C:20]1[CH:21]=[CH:22][C:23]2[N:24]=[CH:25][C:26](=[O:28])[N:17]([CH2:16][CH2:15][N:12]3[CH2:11][CH2:10][CH:9]([NH:8][C:6](=[O:7])[O:5][C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:14][CH2:13]3)[C:18]=2[N:19]=1

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 68810529Ethyl N-[2-({2-[4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1-piperidinyl]ethyl}amino)-6-(methyloxy)-3-pyridinyl]glycinate

Product 1

HCID 57815384tert-Butyl {1-[2-(6-methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)ethyl]piperidin-4-yl}carbamateYield 43.1%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

A solution of ethyl N-[2-({2-[4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1-piperidinyl]ethyl}amino)-6-(methyloxy)-3-pyridinyl]glycinate (1.2 g, 2.7 mmol) in toluene (400 ml) was heated to reflux under argon for 24 hours. This solution was treated at rt with manganese dioxide (2.0 g, 23 mmol). After 7 h the mixture was filtered, washing with warm toluene then evaporated affording a dark oil. Chromatography on silica eluting with 0-100% ethyl acetate in hexane afforded a yellow solid (470 mg, 43%).

Workup

  1. temperatureto reflux under argon for 24 hours
  2. filtrationAfter 7 h the mixture was filtered
  3. washwashing with warm toluene
  4. customthen evaporated
  5. customaffording a dark oil

Sources & evidence

ORD record
ord-e92f874f003640ea9094770f9295b9c0
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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