Hydrochloric Acid → HCID 18975407, compound

HRID 2393370Notes

Reaction equation

HRID 2393370 reaction equation
C([O:5][C:6]([CH2:8][CH:9]1[C:21]2[N:20]3[CH:22]=[CH:23][N:24]=[C:19]3[C:18](=[O:25])[NH:17][C:16]=2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=2)=[O:7])(C)(C)C.CS(C)=O.Cl.C(=O)([O-])O.[Na+]>C(OCC)C.O>[C:6]([CH2:8][CH:9]1[C:21]2[N:20]3[CH:22]=[CH:23][N:24]=[C:19]3[C:18](=[O:25])[NH:17][C:16]=2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=2)([OH:7])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 516892Sodium BicarbonateHCID 18975401HCID 18975401, compound

Product 1

HCID 18975407HCID 18975407, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 1 g of 10-(tert-butoxycarbonyl-methyl)-5H,10H-imidazo[l,2-a]indeno[1,2-e]pyrazin-4-one, 5 ml of dimethyl sulphoxide and 25 ml of 3N hydrochloric acid in ethyl ether is stirred, under cover of argon, for 107 hours at a temperature in the region of 20° C. After concentration under reduced pressure, the residue is crystallized from 30 ml of acetone. The solid obtained is treated with 50 ml of water and 7 ml of saturated sodium hydrogen carbonate solution; three extractions with dichloromethane (3×50 ml) are performed on this mixture, the aqueous phase is filtered and the aqueous solution is acidified with 8 ml of 1N hydrochloric acid. The precipitate formed is filtered off, washed with water and dried at 80° C. under vacuum (1 mmHg; 0.13 kPa) to give 0.35 g of 10-(carboxymethyl)-5H,10H-imidazo[1,2-a]indeno[1,2-e]-pyrazin-4-one in the form of a greenish solid melting above 260° C. (Analysis, % calculated C: 64.05, H: 3.94, N: 14.94, O: 17.06, % found C: 63.7, H: 3.2, N: 14.9).

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe residue is crystallized from 30 ml of acetone
  3. customThe solid obtained
  4. extractionthree extractions with dichloromethane (3×50 ml)
  5. filtrationthe aqueous phase is filtered
  6. customThe precipitate formed
  7. filtrationis filtered off
  8. washwashed with water
  9. customdried at 80° C. under vacuum (1 mmHg; 0.13 kPa)

Sources & evidence

ORD record
ord-2a58d644b0b24de2bd516c13f0c9e438
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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