Pyridine → HCID 59540408, compound

HRID 923425Notes

Reaction equation

HRID 923425 reaction equation
[CH2:1]([NH:3][C@H:4]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH3:2].[C:18](OC(=O)C)(=[O:20])[CH3:19].N1C=CC=CC=1>>[CH2:1]([N:3]([C@H:4]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:9])[CH3:10])=[O:6])[C:18](=[O:20])[CH3:19])[CH3:2]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 59540229HCID 59540229, compound

Product 1

HCID 59540408HCID 59540408, compoundYield 27%

Procedure

A solution of product from Example 122A (0.267 g, 1.135 mmol) in acetic anhydride (1.073 mL, 11.35 mmol) and pyridine (0.918 mL, 11.35 mmol) was stirred at 98° C. for 2 hrs. The mixture was partitioned between CH2Cl2 and 1N HCl solution, and the organic extract was separated, dried over anhydrous sodium sulphate, filtered, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using a solvent gradient of 1-35% ethyl acetate in hexane to give the title compound (0.083 g, 27%).

Workup

  1. customThe mixture was partitioned between CH2Cl2 and 1N HCl solution
  2. extractionthe organic extract
  3. customwas separated
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography on silica gel using a solvent gradient of 1-35% ethyl acetate in hexane

Sources & evidence

ORD record
ord-b1bf8cc0dfaa4358932f4b95e9f3ff4c
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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