Hydrochloric Acid → HCID 18790699, compound

HRID 1075526Notes

Reaction equation

HRID 1075526 reaction equation
[OH-].[Na+].C([O:5][C:6]([CH2:8][CH2:9][C:10]1[CH:31]=[CH:30][C:29]2[C:15]3[NH:16][C:17](=[O:28])[C:18]4[N:19]([CH:20]=[C:21]([C:23]([O:25]CC)=[O:24])[N:22]=4)[C:14]=3[CH2:13][C:12]=2[CH:11]=1)=[O:7])C.O1CCOCC1.Cl>O>[C:6]([CH2:8][CH2:9][C:10]1[CH:31]=[CH:30][C:29]2[C:15]3[NH:16][C:17](=[O:28])[C:18]4[N:19]([CH:20]=[C:21]([C:23]([OH:25])=[O:24])[N:22]=4)[C:14]=3[CH2:13][C:12]=2[CH:11]=1)([OH:7])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 18790688HCID 18790688, compound

Product 1

HCID 18790699HCID 18790699, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

18 ml of 1N sodium hydroxide solution are added, under an argon blanket, to a stirred mixture, at a temperature in the region of 20° C., of 1.75 g of ethyl 8-(2-ethoxycarbonylethyl)-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-2-carboxylate, 220 ml of dioxane and 60 ml of water and stirring is continued for 6 hours. The reaction mixture is filtered, the solid is washed with 2×20 ml of dioxane and 30 ml of water are added to the solid. The solution obtained is acidified to pH 1 with 1N hydrochloric acid and the precipitate is filtered, washed with 2×30 ml of distilled water and then 2×30 ml of acetone and dried under vacuum (1 mm Hg; 0.13 kPa) in the region of 50° C. 0.9 g of 8-(2-carboxyethyl)-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylic acid is obtained in the form of a beige solid melting above 290° C. (1H NMR spectrum in d6-DMSO, T=300K, δ in ppm (200 MHz): 2.60 (2H, t, J=6 Hz, CH2CO2H), 2.90 (2H, t, J=6 Hz, CH2), 4.00 (2H, s, CH2), 7.25 (1H, d, J=8 Hz, arom. CH), 7.45 (1H, s, arom. CH), 7.78 (1H, d, J=8 Hz, arom. CH), 8.50 (1H, s, imidazole H), 12.5 (3H, s, NHCO and 2CO2H)).

Workup

  1. filtrationThe reaction mixture is filtered
  2. washthe solid is washed with 2×20 ml of dioxane and 30 ml of water
  3. additionare added to the solid
  4. customThe solution obtained
  5. filtrationthe precipitate is filtered
  6. washwashed with 2×30 ml of distilled water
  7. dry with material2×30 ml of acetone and dried under vacuum (1 mm Hg; 0.13 kPa) in the region of 50° C

Sources & evidence

ORD record
ord-a53d63bede0e4bcfa26491a2db803375
Source dataset
uspto-grants-1999_05
Patent number
US05902803

Reaction notes

Loading…