HCID 59437390, compound → HCID 59437386, compound

HRID 657073Notes

Reaction equation

HRID 657073 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][CH2:9][C:10](OCC)=[O:11])=[CH:6][CH:5]=[C:4]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[N:3]=1>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][O:15][C:4]2[CH:5]=[CH:6][C:7]3[N:8]=[CH:9][C:10](=[O:11])[NH:1][C:2]=3[N:3]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 1

HCID 59437390HCID 59437390, compound

Product 1

HCID 59437386HCID 59437386, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 1140TolueneSolvent

Procedure

Ethyl N-[2-amino-6-({[4-(methyloxy)phenyl]methyl}oxy)-3-pyridinyl]glycinate (5 g, 15.1 mmol) was dissolved in toluene (500 mL) and heated at reflux for 2.5 days, the reaction was cooled to rt and manganese dioxide (2.4 g, 27.5 mmol) was added. After stirring for 5 h at room temperature 0.8 g of manganese dioxide were added and the reaction was stirred at room temperature overnight. The reaction was filtered through celite and the celite was washed with plenty of 20% methanol/DCM. The solvent were removed and the solid was triturated with diethyl ether, filtered off and washed with more diethyl ether to afford the title compound as a black solid (2.1 g, 50%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2.5 days
  3. additionwere added
  4. filtrationThe reaction was filtered through celite
  5. washthe celite was washed with plenty of 20% methanol/DCM
  6. customThe solvent were removed
  7. customthe solid was triturated with diethyl ether
  8. filtrationfiltered off
  9. washwashed with more diethyl ether

Sources & evidence

ORD record
ord-6f394b6085be4f07bd02d054de2f21b3
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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