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

HRID 225501Notes

Reaction equation

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

Participants

Conditions

Temperature: 20 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-60cc1ec09035441f829e37eee8bc529b
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557105B2

Reaction notes

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