Water → HCID 57642823, compound

HRID 2112905Notes

Reaction equation

HRID 2112905 reaction equation
[Cl:1]N1C(=O)CCC1=O.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:22]2[N:30]=[CH:29][N:28]=[C:27]3[C:23]=2[N:24]=[CH:25][N:26]3[CH3:31])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(OCC)(=O)C.O>CN(C)C=O>[C:9]([O:13][C:14]([N:16]1[CH2:17][CH2:18][N:19]([C:22]2[N:30]=[CH:29][N:28]=[C:27]3[C:23]=2[N:24]=[C:25]([Cl:1])[N:26]3[CH3:31])[CH2:20][CH2:21]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 31398ChlorosuccinimideHCID 11324599HCID 11324599, compound

Product 1

HCID 57642823HCID 57642823, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-chlorosuccinimide (1.25 g) was added to a solution of 4-(9-methyl-9H-purin-6-yl)-piperazine-1-carboxylic acid t-butyl ester (2.70 g) in N,N-dimethylformamide (30 mL), and this was stirred at room temperature for 20 hours. Ethyl acetate (200 mL) and water (50 mL) were added, the organic layer was washed twice with 50 mL of water and then once with 50 mL of saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The organic layer was filtered and then concentrated under reduced pressure. The residue was purified by silica gel chromatography, and the ethyl acetate:hexane 4:1 fraction gave the title compound (1.97 g).

Workup

  1. washthe organic layer was washed twice with 50 mL of water
  2. dry with materialonce with 50 mL of saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
  3. filtrationThe organic layer was filtered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a95f75f465f8412d949b9309392e7548
Source dataset
uspto-grants-2009_04
Patent number
US07524847B2

Reaction notes

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