Pyridine → 2-isopropyl-2-methyl-5H-furo[2,3-b]imidazo[2',1':5,1]pyrrolo[3,4-e]pyridine-3(2H), 5-dione

HRID 580299Notes

Reaction equation

HRID 580299 reaction equation
[CH:1]([C:4]1([CH3:22])[C:8](=[O:9])[NH:7][C:6]([C:10]2[N:15]=[C:14]3[O:16][CH:17]=[CH:18][C:13]3=[CH:12][C:11]=2[C:19](O)=[O:20])=[N:5]1)([CH3:3])[CH3:2].C(OC(=O)C)(=O)C.N1C=CC=CC=1>C(COC)OC>[CH:1]([C:4]1([CH3:22])[C:8](=[O:9])[N:7]2[C:19](=[O:20])[C:11]3[CH:12]=[C:13]4[CH:18]=[CH:17][O:16][C:14]4=[N:15][C:10]=3[C:6]2=[N:5]1)([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 137524676-(4-Isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)furo[2,3-b]pyridine-5-carboxylic acid

Product 1

HCID 138496102-isopropyl-2-methyl-5H-furo[2,3-b]imidazo[2',1':5,1]pyrrolo[3,4-e]pyridine-3(2H), 5-dioneYield 100.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a suspension of 6-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-furo[2,3-b]-pyridine-5-carboxylic acid (11.7 g, 0.039 mol) in 100 mL dimethoxyethane (DME) is added 7.3 mL acetic anhydride and 3.9 mL pyridine. After stirring 24 hours at room temperature, the solids are filtered and washed with ether and the mother liquor is concentrated by adding xylene to aid removal of pyridine. The residue is triturated with ether to obtain solids which are combined with the first crop to give 11.1 g (100%) of product. Recrystallization from 2:1 ethyl acetatehexane gives an analytical sample mp 193°-205° C.

Workup

  1. filtrationthe solids are filtered
  2. washwashed with ether
  3. concentrationthe mother liquor is concentrated
  4. additionby adding xylene
  5. customremoval of pyridine
  6. customThe residue is triturated with ether
  7. customto obtain solids which

Sources & evidence

ORD record
ord-06dc843ddd3145189f0e8e4c8d72cb62
Source dataset
uspto-grants-1988_06
Patent number
US04752323

Reaction notes

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