Water → HCID 178440275, compound

HRID 411578Notes

Reaction equation

HRID 411578 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14]2=[N:15][C:16]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:31])[CH2:29]Cl)=[CH:23][CH:22]=3)=[N:17][C:18](=[O:19])[C:13]2=[C:12]([CH:32]([CH3:34])[CH3:33])[NH:11]1.[NH:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1.O>CN(C=O)C.C1COCC1>[Cl:9][C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:10]1[C:14]2=[N:15][C:16]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28]([CH2:29][N:35]4[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]4)=[O:31])=[CH:23][CH:22]=3)=[N:17][C:18](=[O:19])[C:13]2=[C:12]([CH:32]([CH3:34])[CH3:33])[NH:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 4837PiperazineHCID 178440273HCID 178440273, compound

Product 1

HCID 178440275HCID 178440275, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

Part B: To a stirred solution of 300 mg (0.55 mmol) of 1-(2,4,6-trichlorophenyl)-3-isopropyl-6-(4-(chloroacetamido)benzyl)pyrazolo[3,4-d]pyrimidin-4-one in 6 mL of 1:1 DMF-THF was added 1 g of piperazine. The solution was stirred overnight at ambient temperature and poured into water. The mixture was extracted twice with EtOAc, and the combined organic extracts were washed (brine), dried (MgSO4), and concentrated under reduced pressure to afford 230 mg (71%) of 1-(2,4,6-trichlorophenyl)-3-isopropyl-6-(4-(piperazin-1-ylmethylcarbonylamino)benzyl)pyrazolo[3,4-d]pyrimidin-4-one as an off-white solid. Mass spec.(ESI+): 588((M+H)+).

Workup

  1. extractionThe mixture was extracted twice with EtOAc
  2. washthe combined organic extracts were washed (brine)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-989e1e3571254128baafe1b48edba455
Source dataset
uspto-grants-2003_05
Patent number
US06559152B2

Reaction notes

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