Acetic Acid → HCID 19010359, compound

HRID 1741607Notes

Reaction equation

HRID 1741607 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:13](=[O:14])[N:12]3[C:15](=[O:22])[C:16]([CH3:21])([CH:18]([CH3:20])[CH3:19])[N:17]=[C:11]3[C:7]2=[N:8][C:9]=1[CH3:10])(=[O:3])[CH3:2].[H-].[Na+].[CH2:25]([OH:31])[C:26]1[O:30][CH:29]=[CH:28][CH:27]=1.C(O)(=O)C>O1CCCC1>[C:1]([C:4]1[C:9]([CH3:10])=[N:8][C:7]([C:11]2[NH:12][C:15](=[O:22])[C:16]([CH:18]([CH3:19])[CH3:20])([CH3:21])[N:17]=2)=[C:6]([CH:5]=1)[C:13]([O:31][CH2:25][C:26]1[O:30][CH:29]=[CH:28][CH:27]=1)=[O:14])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7361Furfuryl AlcoholHCID 24758Sodium hydrideHCID 67795870HCID 67795870, compound

Product 1

HCID 19010359HCID 19010359, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.0 g of 7-acetyl-2,8-dimethyl-2-isopropyl-5H-imidazo[1',2':1,2]pyrrolo[3,4-b]-pyridine-3(2H),5-dione in 50 mL tetrahydrofuran is added dropwise to a preformed mixture of 0.03 g sodium hydride and 0.35 mL furfuryl alcohol in 50 mL tetrahydrofuran. The reaction mixture is stirred at room temperature overnight, acidified with acetic acid, and concentrated in vacuo. The residue is chromatographed on silica gel using 5% ethyl acetate in methylene chloride as eluant to afford the desired product. Recrystallization from methylene chloride-hexanes gives a solid, mp 133°-136°.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue is chromatographed on silica gel using 5% ethyl acetate in methylene chloride as eluant

Sources & evidence

ORD record
ord-28a6732243c84e16ac57a479a3f46724
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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