HCID 67351694, compound → HCID 86643702, compound

HRID 1672816Notes

Reaction equation

HRID 1672816 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([N:9]2[CH2:18][C@H:17]3[N:13]([CH2:14][CH2:15][CH2:16]3)[C:12]3[N:19]=[C:20]([S:23][CH3:24])[N:21]=[CH:22][C:11]=3[C:10]2=[O:25])[CH:6]=[CH:7][CH:8]=1>ClCCl.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[CH:4]=[C:5]([N:9]2[CH2:18][C@H:17]3[N:13]([CH2:14][CH2:15][CH2:16]3)[C:12]3[N:19]=[C:20]([S:23][CH3:24])[N:21]=[CH:22][C:11]=3[C:10]2=[O:25])[CH:6]=[CH:7][CH:8]=1)=[O:1]

Participants

4

Reactant 1

HCID 67351694HCID 67351694, compound

Product 1

HCID 86643702HCID 86643702, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

(S)-5-(3-Hydroxymethylphenyl)-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (100 mg, 0.280 mmol) obtained in Step 1 was dissolved in dichloromethane (10 mL), and the mixture was stirred overnight at room temperature after adding manganese dioxide (366 mg, 4.21 mmol). The mixture was filtered through sellite, and the filtrate was collected, concentrated, and purified by silica gel column chromatography to give (S)-5-(3-formylphenyl)-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (77.8 mg, 78%).

Workup

  1. filtrationThe mixture was filtered through sellite
  2. customthe filtrate was collected
  3. concentrationconcentrated
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-96714758cbda4346bb3c8ec75dc8061b
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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