Acetic Acid → Methyl 6-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-furo[2,3-b]pyridine-5-carboxylate

HRID 1906112Notes

Reaction equation

HRID 1906112 reaction equation
[CH:1]([C:4]1([CH3:21])[C:19](=[O:20])[N:7]2[C:8](=[O:18])[C:9]3[CH:10]=[C:11]4[CH:17]=[CH:16][O:15][C:12]4=[N:13][C:14]=3[C:6]2=[N:5]1)([CH3:3])[CH3:2].C[O-].[Na+].[C:25](O)(=[O:27])C>CO>[CH:1]([C:4]1([CH3:21])[C:19](=[O:20])[NH:7][C:6]([C:14]2[N:13]=[C:12]3[O:15][CH:16]=[CH:17][C:11]3=[CH:10][C:9]=2[C:8]([O:27][CH3:25])=[O:18])=[N:5]1)([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 138496102-isopropyl-2-methyl-5H-furo[2,3-b]imidazo[2',1':5,1]pyrrolo[3,4-e]pyridine-3(2H), 5-dione

Product 1

HCID 13752471Methyl 6-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-furo[2,3-b]pyridine-5-carboxylateYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound prepared in Example 40 (10.5 g, 0.037 mol) is suspended in 150 mL absolute methanol and 4.0 g sodium methoxide is added. After stirring for 72 hours at room temperature the mixture is poured onto ice containing acetic acid to maintain the pH at 3-4. A white solid forms and is filtered yielding 9.8 g (84%) of the title compound with mp 134°-137° C.

Workup

  1. additionis poured onto ice
  2. temperatureto maintain the pH at 3-4
  3. filtrationA white solid forms and is filtered

Sources & evidence

ORD record
ord-af5318df6bea46bc844c247836c934c4
Source dataset
uspto-grants-1987_03
Patent number
US04650514

Reaction notes

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