Hydrochloric Acid → HCID 18975452, compound

HRID 2393374Notes

Reaction equation

HRID 2393374 reaction equation
[C:1]([CH:4]([CH:6]1[C:18]2[N:17]3[CH:19]=[CH:20][N:21]=[C:16]3[C:15](=[O:22])[NH:14][C:13]=2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]1=2)[OH:5])([OH:3])=[O:2].[CH3:23][NH:24][C:25](=[O:44])[NH:26]C1C=CC2C3NC(=O)C4N(C=CN=4)C=3CC=2C=1.O.C(O)(=O)C=O.[H-].[Na+].Cl>O.CS(C)=O>[C:1]([CH:4]([CH:6]1[C:18]2[N:17]3[CH:19]=[CH:20][N:21]=[C:16]3[C:15](=[O:22])[NH:14][C:13]=2[C:12]2[CH:11]=[CH:10][C:9]([NH:26][C:25]([NH:24][CH3:23])=[O:44])=[CH:8][C:7]1=2)[OH:5])([OH:3])=[O:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 15620607Glyoxylic acid, monohydrateHCID 18975395HCID 18975395, compoundHCID 18975447HCID 18975447, compound

Product 1

HCID 18975452HCID 18975452, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

The process is performed as in Example 15 for the preparation of 10-(1-carboxy-1-hydroxymethyl)-5H, 10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one but starting with 2 g of 8-(3-methylureido)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one, 32 ml of dimethyl sulphoxide, 0.93 g of glyoxylic acid monohydrate and 1.11 g of sodium hydride. After treatment of the reaction mixture with acetic acid (2.4 ml), the suspension is filtered and 100 ml of acetone are added to the filtrate. The greyish precipitate formed is filtered off, triturated with ethanol (2×50 ml), filtered off and dried at 60° C. under vacuum (1 mmHg; 0.13 kPa). The solid obtained (2.29 g) is treated with 24 ml of water and 12 ml of 1N hydrochloric acid. A brown precipitate forms which is filtered off, washed with water (2×5 ml), then with acetone (2×5 ml) and dried at 60° C. under vacuum (1 mmHg; 0.13 kPa). 1 g of 10-(1-carboxy-1-hydroxymethyl)-8-(3-methylureido)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one is obtained in the form of a dark yellow solid melting above 260° C. (Analysis, % calculated C: 55.28, H: 4.09, N: 18.96, O: 21.66, % found C: 55.1, H: 3.6, N: 18.9).

Workup

  1. filtrationAfter treatment of the reaction mixture with acetic acid (2.4 ml), the suspension is filtered
  2. addition100 ml of acetone are added to the filtrate
  3. customThe greyish precipitate formed
  4. filtrationis filtered off
  5. customtriturated with ethanol (2×50 ml)
  6. filtrationfiltered off
  7. customdried at 60° C. under vacuum (1 mmHg; 0.13 kPa)
  8. customThe solid obtained (2.29 g)
  9. filtrationA brown precipitate forms which is filtered off
  10. washwashed with water (2×5 ml)
  11. dry with materialwith acetone (2×5 ml) and dried at 60° C. under vacuum (1 mmHg; 0.13 kPa)

Sources & evidence

ORD record
ord-64193e18b4d14873a278d311d260d7e1
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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