Methanol → HCID 13246870, compound

HRID 1649873Notes

Reaction equation

HRID 1649873 reaction equation
[H-].[Na+].[CH:3]([C:6]([CH3:21])([N:10]1[C:18](=[O:19])[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20])[C:7]([NH2:9])=[O:8])([CH3:5])[CH3:4].[CH3:22][OH:23]>>[C:7]([C:6]([NH:10][C:11]([C:12]1[N:13]=[CH:14][CH:15]=[CH:16][C:17]=1[C:18]([O:23][CH3:22])=[O:19])=[O:20])([CH3:21])[CH:3]([CH3:5])[CH3:4])(=[O:8])[NH2:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 13246858HCID 13246858, compound

Product 1

HCID 13246870HCID 13246870, compound

Procedure

Sodium hydride (0.47 g of a 50% suspension in mineral oil) is reacted with 500 mL dry methanol under nitrogen. To this is added 51.4 g of 5,7-dihydroalpha-isopropyl-alpha-methyl-5,7-dioxo-6H-pyrrolo [3,4-b]pyridine-6-acetamide and the mixture stired at room temperature overnight. The mixture is concentrated, the residue dissolved in methylene chloride and the solution washed first with 150 mL water followed by 150 mL brine. After drying (Na2SO4), the organic phase is concentrated and the residue crystallized from ether to give 47.85 g of product which is analytically pure mp 108°-145° C. with decomposition.

Workup

  1. concentrationThe mixture is concentrated
  2. dissolutionthe residue dissolved in methylene chloride
  3. washthe solution washed first with 150 mL water
  4. dry with materialAfter drying (Na2SO4)
  5. concentrationthe organic phase is concentrated
  6. customthe residue crystallized from ether

Sources & evidence

ORD record
ord-5dbc30c36cd848059488a2933254a90a
Source dataset
uspto-grants-1990_05
Patent number
US04921961

Reaction notes

Loading…