Trifluoroacetic acid → HCID 22029751, compound

HRID 1792078Notes

Reaction equation

HRID 1792078 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH:9]1[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]1[C:36]2[C:35](=[O:37])[N:34]([CH3:38])[C:33](=[O:39])[N:32]([CH3:40])[C:31]=2[N:30]=[CH:29]1)=O)(C)(C)C.[F:41][C:42]([F:47])([F:46])[C:43]([OH:45])=[O:44]>>[F:41][C:42]([F:47])([F:46])[C:43]([OH:45])=[O:44].[CH3:40][N:32]1[C:31]2[N:30]=[C:29]3[N:28]([C:36]=2[C:35](=[O:37])[N:34]([CH3:38])[C:33]1=[O:39])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[CH2:21][CH:9]1[CH2:10][NH:11][CH2:12][CH2:13][N:8]31

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23536894HCID 23536894, compound

Product 1

HCID 22029751HCID 22029751, compound

Procedure

2-[2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-yl)benzyl]piperazine-1,4-dicarboxylic acid di-tert-butyl ester (0.055 g) was dissolved in trifluoroacetic acid (0.5 ml), the mixture was stirred for 30 minutes, and the solvent was removed by distillation at reduced pressure. The residue was dissolved in N,N-dimethylformamide, and N-chlorosuccinimide (0.025 g) was added to the solution. The mixture was stirred at room temperature for 14 hours, 1,8-diazabicyclo-[5,4,0]-7-undecene (0.050 ml) was added thereto, and was further stirred for 1 hour. After removing the solvent by distillation at reduced pressure, the residue was purified by HPLC with a reversed phase column using water-acetonitrile-trifluoroacetic acid system as elution solvent to give 0.0079 g of the title compound.

Workup

  1. customthe solvent was removed by distillation at reduced pressure
  2. dissolutionThe residue was dissolved in N,N-dimethylformamide
  3. additionN-chlorosuccinimide (0.025 g) was added to the solution
  4. stirringThe mixture was stirred at room temperature for 14 hours
  5. addition1,8-diazabicyclo-[5,4,0]-7-undecene (0.050 ml) was added
  6. stirringwas further stirred for 1 hour
  7. customAfter removing the solvent
  8. distillationby distillation at reduced pressure
  9. customthe residue was purified by HPLC with a reversed phase column
  10. washas elution solvent

Sources & evidence

ORD record
ord-ab99aab08c6b4fb0ae2b6f9fa5a52a16
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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