Hydrochloric Acid → HCID 9862994, compound

HRID 1974621Notes

Reaction equation

HRID 1974621 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)[C:7]([F:17])=[CH:6][C:5]=1[NH:18][C:19]([NH2:21])=[O:20])[CH3:2].C[O-].[Na+].[C:25](OCC)(=O)[CH2:26][C:27](OCC)=[O:28].Cl>CO>[CH2:1]([N:3]1[C:4]2[CH:9]=[C:8]([N:10]3[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]3)[C:7]([F:17])=[CH:6][C:5]=2[N:18]2[C:19](=[O:20])[NH:21][C:27](=[O:28])[CH:26]=[C:25]12)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 10942334Sodium MethoxideHCID 15751490HCID 15751490, compound

Product 1

HCID 9862994HCID 9862994, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-[2-(N-ethylamino)-5-fluoro-4-(4-methyl-1-piperazinyl]phenyl-urea (640 mg) in methanol is treated with a freshly prepared methanolic solution of sodium methylate (from 150 mg of sodium) and heated under reflux for a short time. After cooling the solution is treated with diethyl malonate and stirred for 6 hours. The solution obtained is poured into a mixture of ice and 2N HCl (50 ml). The methanol is evaporated and the aqueous phase is extracted with ethyl acetate (3×100 ml) and methylene chloride (2×100 ml). After drying over magnesium sulfate the solvent mixture is evaporated and the residue is suspended in a small amount of cold ethyl acetate and filtered off. There are obtained 130 mg (17%) of 5-ethyl-8-fluoro-7-(4-methyl-1-piperazinyl)pyrimido[1,6-a]benzimidazole-1,3(2H,5H)-dione.

Workup

  1. temperatureheated
  2. temperatureunder reflux for a short time
  3. temperatureAfter cooling the solution
  4. customThe solution obtained
  5. customThe methanol is evaporated
  6. extractionthe aqueous phase is extracted with ethyl acetate (3×100 ml) and methylene chloride (2×100 ml)
  7. dry with materialAfter drying over magnesium sulfate the solvent mixture
  8. customis evaporated
  9. filtrationfiltered off

Sources & evidence

ORD record
ord-d551e6924cad46abb3df3db62fc70188
Source dataset
uspto-grants-1994_02
Patent number
US05283248

Reaction notes

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