Sodium Hydroxide → HCID 18790667, compound

HRID 1107047Notes

Reaction equation

HRID 1107047 reaction equation
[OH-].[Na+].C([O:5][C:6]([CH:8]([C:10]1[C:11]2[CH2:12][C:13]3[N:18]4[CH:19]=[C:20]([C:22]([O:24]CC)=[O:23])[N:21]=[C:17]4[C:16](=[O:27])[NH:15][C:14]=3[C:28]=2[CH:29]=[CH:30][CH:31]=1)[CH3:9])=[O:7])C>O1CCOCC1>[C:6]([CH:8]([C:10]1[C:11]2[CH2:12][C:13]3[N:18]4[CH:19]=[C:20]([C:22]([OH:24])=[O:23])[N:21]=[C:17]4[C:16](=[O:27])[NH:15][C:14]=3[C:28]=2[CH:29]=[CH:30][CH:31]=1)[CH3:9])([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18790651HCID 18790651, compound

Product 1

HCID 18790667HCID 18790667, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

19 ml of 1N sodium hydroxide solution are added dropwise, under a stream of nitrogen and at a temperature in the region of 20° C., to a suspension of 1.9 g of ethyl 9-(1-ethoxycarbonylethyl)-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-2-carboxylate in a mixture of dioxane (245 ml) and distilled water (65 ml). The reaction is continued for 4 hours and 30 minutes at the same temperature. The insoluble material, formed after partial evaporation of the solvents, is filtered, washed with water and then with a mixture of dimethylformamide (10 ml) and methanol (80 ml), and dried. The solid is dissolved in 20 ml of 1N sodium hydroxide solution and stirred for 4 hours at a temperature in the region of 20° C. The reaction mixture is then treated with 1N hydrochloric acid to pH 1 and the precipitate formed is filtered, washed with water and then with acetone and dried to result in 0.62 g of the hydrate of 9-(1-carboxyethyl)-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-2-carboxylic acid in the form of a pink powder, the melting point of which is greater than 260° C. (Analysis C17H13N3O5.1.4H2O; % Calculated C: 60.18, H: 3.86, N: 12.38; % Found C: 60.1, H: 3.2, N: 12.5; 1H NMR spectrum in d6-DMSO, T=300 K, δ in ppm (300 MHz): 1.5 (3H, CH3), 3.9 (1H, CH), 4.1 (2H, CH2), 7.3, 7.5, 7.9 (each 1H, 3 arom. CH), 8.6 (1H, imidazole CH), between 12 and 13.5 (3H, 2 COOH and NHCO)).

Workup

  1. distillationdistilled water (65 ml)
  2. customThe insoluble material, formed
  3. customafter partial evaporation of the solvents
  4. filtrationis filtered
  5. washwashed with water
  6. additionwith a mixture of dimethylformamide (10 ml) and methanol (80 ml)
  7. customdried
  8. dissolutionThe solid is dissolved in 20 ml of 1N sodium hydroxide solution
  9. additionThe reaction mixture is then treated with 1N hydrochloric acid to pH 1
  10. customthe precipitate formed
  11. filtrationis filtered
  12. washwashed with water
  13. dry with materialwith acetone and dried

Sources & evidence

ORD record
ord-e39ce34aeb0e4f999e666dfe12dbc9dd
Source dataset
uspto-grants-2000_05
Patent number
US06057454

Reaction notes

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