HCID 58424856, compound → HCID 58424889, compound

HRID 2409431Notes

Reaction equation

HRID 2409431 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:22]=[CH:21][C:8]2[N:9]([CH2:18][O:19][CH3:20])[C:10](=[O:17])[C:11]3[CH:12]=[CH:13][CH:14]=[N:15][C:16]=3[C:7]=2[CH:6]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH3:20][O:19][CH2:18][N:9]1[C:8]2[CH:21]=[CH:22][C:5]([CH2:4][CH2:3][CH:2]=[O:1])=[CH:6][C:7]=2[C:16]2[N:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]1=[O:17]

Participants

4

Reactant 2

HCID 58424856HCID 58424856, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 58424889HCID 58424889, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (200 mg, 0.67 mmol) prepared in step 6 was dissolved in dichloromethane, added with pyridinium chlorochromate (289 mg, 1.34 mmol) and silica gel (289 mg) at room temperature. The resulting mixture was stirred for 2 hours at room temperature and filtered to remove silica gel. The filtrate was extracted with dichloromethane, dried over anhydrous magnesium sulfate and concentrated to dryness. The residue was then purified by flash column chromatography (chloroform:methanol=15:1) to obtain the title compound (151 mg, yield: 76%, white solid).

Workup

  1. filtrationfiltered
  2. customto remove silica gel
  3. extractionThe filtrate was extracted with dichloromethane
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated to dryness
  6. customThe residue was then purified by flash column chromatography (chloroform:methanol=15:1)

Sources & evidence

ORD record
ord-eb57f28766c641d38dcc487c25ea8bc7
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

Loading…