Ethyl Acetate → Imatinib (Pyridine)-N-oxide

HRID 225500Notes

Reaction equation

HRID 225500 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl[CH2:9][C:10]1[CH:39]=[CH:38][C:13]([C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([NH:24][C:25]3[N:30]=[C:29]([C:31]4[CH:32]=[N+:33]([O-:37])[CH:34]=[CH:35][CH:36]=4)[CH:28]=[CH:27][N:26]=3)[CH:18]=2)=[O:15])=[CH:12][CH:11]=1.C(OCC)(=O)C>C(O)C>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([NH:24][C:25]4[N:30]=[C:29]([C:31]5[CH:32]=[N+:33]([O-:37])[CH:34]=[CH:35][CH:36]=5)[CH:28]=[CH:27][N:26]=4)[CH:18]=3)=[O:15])=[CH:38][CH:39]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 531671-MethylpiperazineHCID 68489405HCID 68489405, compound

Product 1

HCID 9827642Imatinib (Pyridine)-N-oxide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
10 °C

Procedure

N-Methylpiperazine (99 mg, 1.0 mmol) is added to a stirred suspension of 4-chloromethyl-N-[4-methyl-3-[[4-(1-oxido-3-pyridinyl)-2-pyrimidinyl]-amino]-phenyl]-benzamide (220 mg, 0.49 mmol) In ethanol (5 mL). The mixture is then stirred at 10° C. for 15 h to give a solution, which is then cooled to RT and treated with ethyl acetate (200 mL). The resulting solution is washed with aqueous sodium hydroxide (100 mL of 2M) and saturated aqueous sodium chloride solution (100 mL), dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by column chromatography on silica gel, eluent 25% aqueous ammonia-methanol-dichloromethane (0.5:10:90) to give the title compound as a yellow crystalline solid, m.p. 232-235° C.

Workup

  1. customto give a solution, which
  2. temperatureis then cooled to RT
  3. washThe resulting solution is washed with aqueous sodium hydroxide (100 mL of 2M) and saturated aqueous sodium chloride solution (100 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent is evaporated off under reduced pressure
  7. customto yield the crude product which
  8. customis purified by column chromatography on silica gel, eluent 25% aqueous ammonia-methanol-dichloromethane (0.5:10:90)

Sources & evidence

ORD record
ord-fb62a2f977a04b689846f3cfbaee395e
Source dataset
uspto-grants-2009_07
Patent number
US07557105B2

Reaction notes

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