Sodium Hydroxide → HCID 18790664, compound

HRID 1075527Notes

Reaction equation

HRID 1075527 reaction equation
[OH-].[Na+].[CH3:3][NH:4][C:5]([CH2:7][C:8]1[C:9]2[CH2:10][C:11]3[N:16]4[CH:17]=[C:18]([C:20]([O:22]CC)=[O:21])[N:19]=[C:15]4[C:14](=[O:25])[NH:13][C:12]=3[C:26]=2[CH:27]=[CH:28][CH:29]=1)=[O:6]>O1CCOCC1>[CH3:3][NH:4][C:5]([CH2:7][C:8]1[C:9]2[CH2:10][C:11]3[N:16]4[CH:17]=[C:18]([C:20]([OH:22])=[O:21])[N:19]=[C:15]4[C:14](=[O:25])[NH:13][C:12]=3[C:26]=2[CH:27]=[CH:28][CH:29]=1)=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18790720HCID 18790720, compound

Product 1

HCID 18790664HCID 18790664, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

8.2 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 g of ethyl 9-(N-methylaminocarbonylmethyl)-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-2-carboxylate in a dioxane distilled water (100/27 by volume) mixture. The reaction is continued for 2 hours at the same temperature. The light-grey insoluble material is filtered, washed with acetone and then taken up in 15 ml of distilled water. This aqueous solution is filtered and then acidified to pH 1 with N hydrochloric acid. The precipitate formed is filtered and washed with water, with acetone and then with ethyl ether to result in 0.59 g of the trihydrate of 9-(N-methylaminocarbonylmethyl)-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-2-carboxylic acid in the form of a white powder, the melting point of which is greater than 260° C. (Analysis C17H14N4O4.3H2O; % Calculated C: 60.35, H: 4.17, N: 16.56; % Found C: 60.0, H: 4.1, N: 16.3; 1H NMR spectrum in CD3CO2D, T=300K, δ in ppm (300 MHz): 2.7 (3H, s, NCH3), 3.9 (2H, s, CH2CO), 4.1 (2H, s, CH2), 7.2 (1H, d, J=8 Hz, arom. CH), 7.4 (1H, t, J=8 Hz, arom. CH), 7.7 (1H, d, J=8 Hz, arom. CH), 8.5 (1H, s, imidazole H)).

Workup

  1. distillationdistilled water (100/27 by volume) mixture
  2. filtrationThe light-grey insoluble material is filtered
  3. washwashed with acetone
  4. filtrationThis aqueous solution is filtered
  5. customThe precipitate formed
  6. filtrationis filtered
  7. washwashed with water, with acetone

Sources & evidence

ORD record
ord-9b691874fa2a47cbbd389824ed315c0b
Source dataset
uspto-grants-1999_05
Patent number
US05902803

Reaction notes

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