Hydrogen Bromide → HCID 18694083, compound

HRID 1870810Notes

Reaction equation

HRID 1870810 reaction equation
C([O:3][P:4]([CH2:9][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)([O:6]CC)=[O:5])C.Br.O>C(O)(=O)C>[O:27]=[C:16]1[NH:15][C:14]2[C:28]3[CH:29]=[CH:30][CH:31]=[C:10]([CH2:9][P:4]([OH:6])([OH:5])=[O:3])[C:11]=3[CH2:12][C:13]=2[N:18]2[CH:19]=[C:20]([C:22]([OH:24])=[O:23])[N:21]=[C:17]12

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 18694057HCID 18694057, compound

Product 1

HCID 18694083HCID 18694083, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.6 g of ethyl 9-(diethoxyphosphorylmethyl)-4-oxo-5,10-dihydroimidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate, 30 ml of hydrobromic acid at 30% in acetic acid and 10 ml of distilled water is heated at reflux for 2 hours. The reaction mixture is filtered and the solid is washed with 3×20 ml of distilled water, and then with 2×10 ml of acetone and finally dried under vacuum (1 mm Hg, 0.13 kPa) at close to 40° C. 0.3 g of 4-oxo-9-phosphonomethyl-5,10-dihydroimidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylic acid is obtained in the form of a beige solid melting above 260° C. [Analysis: C15H12N3O6P, 0.09 HBr, 0.38 HCl, 1.54 H2O, % calculated C: 49.87, H: 3.3, N: 11.63, O: 26.57, P: 8.57, % found C: 49.8, H: 3.4, N: 11.1].

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe reaction mixture is filtered
  3. washthe solid is washed with 3×20 ml of distilled water
  4. dry with materialwith 2×10 ml of acetone and finally dried under vacuum (1 mm Hg, 0.13 kPa)
  5. customat close to 40° C

Sources & evidence

ORD record
ord-cc5b763168d84282b70952b604519fb2
Source dataset
uspto-grants-2000_08
Patent number
US06100264

Reaction notes

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