HCID 117737276, compound → HCID 117736967, compound

HRID 1504389Notes

Reaction equation

HRID 1504389 reaction equation
[CH2:1]([S:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]([C:19]1[C:24]([O:25][CH3:26])=[CH:23][C:22]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([CH3:34])[CH:28]=3)=[C:21]([F:35])[CH:20]=1)[C:14](=[O:36])[CH2:13][NH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CN(C=O)C.[O-2].[O-2].[Mn+4]>[CH2:1]([S:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]([C:19]1[C:24]([O:25][CH3:26])=[CH:23][C:22]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([CH3:34])[CH:28]=3)=[C:21]([F:35])[CH:20]=1)[C:14](=[O:36])[CH:13]=[N:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 117737276HCID 117737276, compound

Product 1

HCID 117736967HCID 117736967, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-(benzylthio)-1-(4′-chloro-2-fluoro-5-methoxy-3′-methyl-[1,1′-biphenyl]-4-yl)-3,4-dihydroquinoxalin-2(1H)-one (1.43 g, 2.76 mmol), and manganese dioxide (0.095 ml, 5.51 mmol) in DMF (13.78 ml) was stirred at room temperature for 4 hour. The reaction mixture was filtered through Celite, washed with methanol and the solvent was removed. The residue was purified using Biotage, eluting with a 0-50% ethyl acetate in hexane gradient, to afford 6-(benzylthio)-1-(4′-chloro-2-fluoro-5-methoxy-3′-methyl-[1,1′-biphenyl]-4-yl)quinoxalin-2(1H)-one (0.897 g, 1.735 mmol, 63.0% yield). m/z (ESI) 518.2 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashed with methanol
  3. customthe solvent was removed
  4. customThe residue was purified
  5. washeluting with a 0-50% ethyl acetate in hexane gradient

Sources & evidence

ORD record
ord-25223ad2877a4175a259c8aba6a1236b
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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