3-Oxo-2,3,4,4a, 5,6,8,9-octahydro-1,2,7-triaza-benzocycloheptene-7-carboxylic acid tert-butyl ester → tert-Butyl 3-oxo-2,3,5,6,8,9-hexahydro-7H-pyridazino[3,4-d]azepine-7-carboxylate

HRID 239163Notes

Reaction equation

HRID 239163 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2=[N:15][NH:16][C:17](=[O:19])[CH2:18][CH:11]2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2=[N:15][NH:16][C:17](=[O:19])[CH:18]=[C:11]2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 866865123-Oxo-2,3,4,4a, 5,6,8,9-octahydro-1,2,7-triaza-benzocycloheptene-7-carboxylic acid tert-butyl ester

Product 1

HCID 86686513tert-Butyl 3-oxo-2,3,5,6,8,9-hexahydro-7H-pyridazino[3,4-d]azepine-7-carboxylateYield 79.2%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

7 g 3-oxo-2,3,4,4a, 5,6,8,9-octahydro-1,2,7-triaza-benzocycloheptene-7-carboxylic acid tert-butyl ester was dissolved in 70 mL toluene and 6.7 g manganese dioxide was added to the reaction mixture. It was heated at reflux for 48 h. After completion of the reaction, the reaction mixture was diluted with chloroform and filtered through celite. The filtrate was concentrated and purified by column chromatography to afford 5.5 g of the desired product. (M+H)+=266

Workup

  1. temperatureIt was heated
  2. temperatureat reflux for 48 h
  3. customAfter completion of the reaction
  4. filtrationfiltered through celite
  5. concentrationThe filtrate was concentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-b4b091f182684dce8868f11e52bdc5ef
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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