Hydrochloric Acid → Pyrimido(1,6-a)benzimidazole-1,3(2H,5H)-dione, 5-cyclopropyl-8-fluoro-2-hydroxy-7-(1-piperazinyl)-, monohydrochloride

HRID 1974632Notes

Reaction equation

HRID 1974632 reaction equation
[CH:1]1([N:4]2[C:8]3[CH:9]=[C:10]([N:14]4[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]4)[C:11]([F:13])=[CH:12][C:7]=3[N:6]3[C:27](=[O:33])[N:28]([OH:32])[C:29](=[O:31])[CH:30]=[C:5]23)[CH2:3][CH2:2]1.[ClH:34]>O1CCOCC1>[ClH:34].[CH:1]1([N:4]2[C:8]3[CH:9]=[C:10]([N:14]4[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]4)[C:11]([F:13])=[CH:12][C:7]=3[N:6]3[C:27](=[O:33])[N:28]([OH:32])[C:29](=[O:31])[CH:30]=[C:5]23)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15751521HCID 15751521, compound

Product 1

HCID 3071578Pyrimido(1,6-a)benzimidazole-1,3(2H,5H)-dione, 5-cyclopropyl-8-fluoro-2-hydroxy-7-(1-piperazinyl)-, monohydrochlorideYield 58%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 4-[5-cyclopropyl-8-fluoro-1,2,3,5-tetrahydro-2-hydroxy-1,3-dioxopyrimido[1,6-a]benzimidazol-7-yl]-1-piperazinecarboxylate (350 mg, 0.76 mmol) is treated with a 2.5N hydrochloric acid solution in dioxane (4 ml), whereby a white precipitate forms immediately. The suspension is stirred at room temperature (25°) for 18 hours. The separated crystals are filtered off and dissolved in water (10 ml). The solution is treated with active charcoal, then filtered and cooled to 0°. The separated crystals are filtered off, washed with ethanol and ether and dried in a high vacuum. There are obtained 176 mg (58%) of 5-cyclopropyl-8-fluoro-2-hydroxy-7-(1-piperazinyl)-pyrimido[1,6-a]benzimidazole-1,3(2H,5H)-dione hydrochloride.

Workup

  1. filtrationThe separated crystals are filtered off
  2. dissolutiondissolved in water (10 ml)
  3. additionThe solution is treated with active charcoal
  4. filtrationfiltered
  5. temperaturecooled to 0°
  6. filtrationThe separated crystals are filtered off
  7. washwashed with ethanol and ether
  8. customdried in a high vacuum

Sources & evidence

ORD record
ord-3cfdb0329c0042cba4b11edc411d7eed
Source dataset
uspto-grants-1994_02
Patent number
US05283248

Reaction notes

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