Sodium Hydroxide → 4-((4-Methyl-1,4-dioxido-1-piperazinyl)methyl)-N-(4-methyl-3-((4-(3-pyridinyl)-2-pyrimidinyl)amino)phenyl)benzamide

HRID 225501

반응식

HRID 225501 반응식
CS(O)(=O)=[O:3].[CH3:6][N:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:42]=[CH:41][C:17]([C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([NH:28][C:29]4[N:34]=[C:33]([C:35]5[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=5)[CH:32]=[CH:31][N:30]=4)[CH:22]=3)=[O:19])=[CH:16][CH:15]=2)[CH2:9][CH2:8]1.[OH-:43].[Na+]>OO>[CH3:6][N+:7]1([O-:3])[CH2:12][CH2:11][N+:10]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([NH:28][C:29]4[N:34]=[C:33]([C:35]5[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=5)[CH:32]=[CH:31][N:30]=4)[CH:22]=3)=[O:19])=[CH:41][CH:42]=2)([O-:43])[CH2:9][CH2:8]1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 123596Imatinib Mesylate

생성물 1

HCID 717494574-((4-Methyl-1,4-dioxido-1-piperazinyl)methyl)-N-(4-methyl-3-((4-(3-pyridinyl)-2-pyrimidinyl)amino)phenyl)benzamide

시약·촉매·용매 1

HCID 784Hydrogen Peroxide용매

반응 조건

온도
20 °C

실험 절차

4-[(4-Methyl-1-piperazinyl)-methyl]-N-{4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]-amino]-phenyl}-benzamide monomethanesulphonate (3.00 g, 5 mmol; prepared as described in WO 99/03854) is added to aqueous hydrogen peroxide (30 mL of 3%) and the resulting solution is stirred at 20° C. for 160 h. The pH of the solution is then adjusted to pH 14 with aqueous sodium hydroxide (4 M) and the resulting suspension is stirred for 1.5 h. The crude product is filtered off, washed with water, dried and purified by column chromatography on silica gel, eluent 25% aqueous ammonia-ethanol-dichloromethane (5:30:70), to give the title compound as a yellow crystalline solid, m.p. 242-244° C.

후처리

  1. stirringthe resulting suspension is stirred for 1.5 h
  2. filtrationThe crude product is filtered off
  3. washwashed with water
  4. customdried
  5. custompurified by column chromatography on silica gel, eluent 25% aqueous ammonia-ethanol-dichloromethane (5:30:70)

출처 및 근거

ORD 기록
ord-60cc1ec09035441f829e37eee8bc529b
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557105B2

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