Water → HCID 57642834, compound

HRID 2112907Notes

Reaction equation

HRID 2112907 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:22]=[CH:21][N:20]=[C:19]3[C:15]=2[N:16]=[CH:17][N:18]3[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]#[N:31])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:32]N1C(=O)CCC1=O.C(OCC)(=O)C.O>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[N:22]=[CH:21][N:20]=[C:19]3[C:15]=2[N:16]=[C:17]([Cl:32])[N:18]3[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]#[N:31])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 31398Chlorosuccinimide2×HCID 576428714-[9-(2-Cyanobenzyl)-9H-purin-6-yl]-piperazine-1-carboxylic acid t-butyl ester

Product 1

HCID 57642834HCID 57642834, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[9-(2-Cyanobenzyl)-9H-purin-6-yl]-piperazine-1-carboxylic acid t-butyl ester (0.419 g) was suspended in N,N-dimethylformamide (80 mL), and then N-chlorosuccinimide (0.160 g) was added. This was stirred at room temperature for 72 hours. N-chlorosuccinimide (0.160 g) was added again, and this was then heated at 60° C. for 18 hours. Ethyl acetate (200 mL) and water (100 mL) were then added, and the organic layer was washed twice with 50 mL of water and then once with 5 mL of saturated aqueous sodium chloride solution. This was then dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure, and then the residue was purified by silica gel chromatography. The dichloromethane:ethyl acetate 7:3 fraction gave the title compound (0.100 g).

Workup

  1. temperaturethis was then heated at 60° C. for 18 hours
  2. washthe organic layer was washed twice with 50 mL of water
  3. dry with materialThis was then dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-85d7d6f867e84f0eadb21bd9c11486dd
Source dataset
uspto-grants-2009_04
Patent number
US07524847B2

Reaction notes

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