Trifluoroacetic acid → Pyrimido(1,6-a)benzimidazole-1,3(2H,5H)-dione, 5-cyclopropyl-8-fluoro-7-(1-piperazinyl)-, mono(trifluoroacetate)

HRID 1974627Notes

Reaction equation

HRID 1974627 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:32])[NH:28][C:29](=[O:31])[CH:30]=[C:5]23)[CH2:3][CH2:2]1.C(=O)([O-])O.[Na+].[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41]>>[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41].[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:32])[NH:28][C:29](=[O:31])[CH:30]=[C:5]23)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 15751512HCID 15751512, compound

Product 1

HCID 3071576Pyrimido(1,6-a)benzimidazole-1,3(2H,5H)-dione, 5-cyclopropyl-8-fluoro-7-(1-piperazinyl)-, mono(trifluoroacetate)Yield 60.6%

Procedure

tert-Butyl 4-[5-cyclopropyl-8-fluoro-1,2,3,5-tetrahydro-1,3-dioxopyrimido[1,6-a]benzimidazol-7-yl]-1-piperazinecarboxylate (471 mg, 1 mmol) is dissolved in trifluoroacetic acid (2 ml). After 1 hour at 25° the trifluoroacetic acid is distilled off. The residue is taken up in water (10 ml), treated with sodium hydrogen carbonate (168 mg, 2 mmol) and stirred at 25° for 2 hours. The suspension is cooled to 0°. The crystals are filtered off, washed in succession with in each case 5 ml of cold water and ethanol and recrystallized from ethanol/water (95/5). There are obtained 208 mg (60.6%) of 5-cyclopropyl-8-fluoro-7-(1-piperazinyl)-pyrimido[1,6-a]benzimidazole-1,3(2H,5H)-dione trifluoroacetate.

Workup

  1. distillationAfter 1 hour at 25° the trifluoroacetic acid is distilled off
  2. temperatureThe suspension is cooled to 0°
  3. filtrationThe crystals are filtered off
  4. washwashed in succession with in each case 5 ml of cold water and ethanol
  5. customrecrystallized from ethanol/water (95/5)

Sources & evidence

ORD record
ord-69597b1bb750454db8b095624f83f298
Source dataset
uspto-grants-1994_02
Patent number
US05283248

Reaction notes

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