Piperazine → Cgp-74588

HRID 1793649Notes

Reaction equation

HRID 1793649 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[CH2:8][C:9]1[CH:37]=[CH:36][C:12]([C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([NH:23][C:24]3[N:29]=[C:28]([C:30]4[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=4)[CH:27]=[CH:26][N:25]=3)[CH:17]=2)=[O:14])=[CH:11][CH:10]=1>C(O)C.O>[CH3:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:13](=[O:14])[C:12]2[CH:11]=[CH:10][C:9]([CH2:8][N:1]3[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]3)=[CH:37][CH:36]=2)=[CH:17][C:18]=1[NH:23][C:24]1[N:29]=[C:28]([C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[CH:27]=[CH:26][N:25]=1

Participants

5

Reactant 2

HCID 4837PiperazineHCID 101810754-(Chloromethyl)-N-(4-methyl-3-((4-(3-pyridinyl)-2-pyrimidinyl)amino)phenyl)benzamide

Product 1

HCID 9869737Cgp-74588

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

25.8 g (300 mmol) of piperazine are suspended in a mixture of 25 ml of ethanol and 25 ml of water. After almost a clear solution has formed, 12.9 g (30 mmol) of 4-chloromethyl-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-benzamide are added step by step. The yellow solution is boiled under reflux for 14 hours, cooled to room, temperature and filtered over Celite. 100 ml of water is added to the solution, the ethanol is evaporated under vacuum and 30 ml of 1N NaOH is added, leading to crystallization of the product. Drying at 50 mbar and 60° C. yields N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-4-piperazin-1-ylmethyl-benzamide; Rf=0.15 (methylene chloride:ethyl acetate:methanol:conc. aqueous ammonium hydroxide solution=60:10:30:2); tR (HPLC)2) 14.6 min.

Workup

  1. customAfter almost a clear solution has formed
  2. temperatureunder reflux for 14 hours
  3. temperaturecooled to room, temperature
  4. filtrationfiltered over Celite
  5. addition100 ml of water is added to the solution
  6. customthe ethanol is evaporated under vacuum and 30 ml of 1N NaOH
  7. additionis added
  8. customleading to crystallization of the product
  9. customDrying at 50 mbar and 60° C.

Sources & evidence

ORD record
ord-5a591d52583e406b91b766cc7f618e39
Source dataset
uspto-grants-2006_07
Patent number
US07081532B2

Reaction notes

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