HCID 117842960, compound → HCID 117844058, compound

HRID 2209255Notes

Reaction equation

HRID 2209255 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:14][C@@H:15]([C@@H:17]2[CH2:21][C:20](=[O:22])[N:19]([C@@H:23]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[CH3:24])[CH2:18]2)[CH3:16])[C:5]2[N:6]([N:8]=[CH:9][C:10]=2/[CH:11]=[N:12]/O)[CH:7]=1>C(OC(=O)C)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:14][C@@H:15]([C@@H:17]2[CH2:21][C:20](=[O:22])[N:19]([C@@H:23]([C:25]3[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)[CH3:24])[CH2:18]2)[CH3:16])[C:5]2[N:6]([N:8]=[CH:9][C:10]=2[C:11]#[N:12])[CH:7]=1

Participants

3

Reactant 1

HCID 117842960HCID 117842960, compound

Product 1

HCID 117844058HCID 117844058, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To an appropriate sized microwave vial, crude (E)-6-bromo-4-((R)-1-((R)-1-((R)-1-(4-methoxyphenyl)ethyl)-5-oxopyrrolidin-3-yl)ethoxy)pyrazolo[1,5-a]pyridine-3-carbaldehyde oxime (511 mg, 1.02 mmol) was heated in acetic anhydride (5.0 mL) at 100° C. for 24 h. The reaction was concentrated under reduced pressure, neutralized with a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were washed with brine, dried, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to afford 6-bromo-4-((R)-1-((R)-1-((R)-1-(4-methoxyphenyl)ethyl)-5-oxopyrrolidin-3-yl)ethoxy)pyrazolo[1,5-a]pyridine-3-carbonitrile.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-d0ccca27d898429ba47877b011092d85
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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