HCID 131729213, compound → HCID 131729212, compound

HRID 1801853Notes

Reaction equation

HRID 1801853 reaction equation
[Cl:1][C:2]1[C:3]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:18]2[CH2:23][CH2:22][N:21]([C:24](=[O:26])[CH3:25])[CH2:20][CH2:19]2)=[N:4][CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1>C(OCC)(=O)C>[NH2:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:18]2[CH2:19][CH2:20][N:21]([C:24](=[O:26])[CH3:25])[CH2:22][CH2:23]2)=[N:4][CH:5]=1

Participants

3

Reactant 1

HCID 131729213HCID 131729213, compound

Product 1

HCID 131729212HCID 131729212, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Compound of step i (3.15 g, 8.34 mmol) was dissolved in ethyl acetate (50 mL). Stannous chloride dihydrate (7.52 g, 33.36 mmol) was added at room temperature (25° C.) and stirring was continued for 18 hours. Solvent was removed under vacuum and chloroform (50 mL) was added. 1 N sodium hydroxide solution was added until a clear solution was obtained. Separated the organic layer was separated and extracted with chloroform. The chloroform layer was washed with brine & water successively, dried over sodium sulfate and concentrated under vacuum to obtain crude product that was further purified by column chromatography (silica gel—˜200 mesh, 1% methanol in chloroform) to obtain the title compound.

Workup

  1. customSolvent was removed under vacuum and chloroform (50 mL)
  2. additionwas added
  3. addition1 N sodium hydroxide solution was added until a clear solution
  4. customwas obtained
  5. customSeparated the organic layer
  6. customwas separated
  7. extractionextracted with chloroform
  8. washThe chloroform layer was washed with brine & water successively
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated under vacuum
  11. customto obtain crude product that
  12. customwas further purified by column chromatography (silica gel—˜200 mesh, 1% methanol in chloroform)

Sources & evidence

ORD record
ord-04f0da5ebcbf4afda9b5c1ab37d23b2c
Source dataset
uspto-grants-2013_01
Patent number
US08349862B2

Reaction notes

Loading…