Ethyl Acetate → Imatinib (Pyridine)-N-oxide

HRID 225500ノート

反応式

HRID 225500 の反応式
[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

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 531671-MethylpiperazineHCID 68489405HCID 68489405、化合物

生成物 1

HCID 9827642Imatinib (Pyridine)-N-oxide

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
10 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-fb62a2f977a04b689846f3cfbaee395e
出典データセット
uspto-grants-2009_07
特許番号
US07557105B2

反応ノート

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