Imatinib → 4-[(4-Methyl-4-oxo-4lambda~5~-piperazin-1-yl)methyl]-N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)benzamide

HRID 225499Notes

Reaction equation

HRID 225499 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:48]=[CH:47][C:23]([C:24]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([NH:34][C:35]4[N:40]=[C:39]([C:41]5[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=5)[CH:38]=[CH:37][N:36]=4)[CH:28]=3)=[O:25])=[CH:22][CH:21]=2)[CH2:15][CH2:14]1>ClCCl>[CH3:12][N+:13]1([O-:6])[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:24]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([NH:34][C:35]4[N:40]=[C:39]([C:41]5[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=5)[CH:38]=[CH:37][N:36]=4)[CH:28]=3)=[O:25])=[CH:47][CH:48]=2)[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 5291ImatinibHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 299822684-[(4-Methyl-4-oxo-4lambda~5~-piperazin-1-yl)methyl]-N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperoxybenzoic acid (Fluka, Buchs, Switzerland; 2.06 g of 55%, 4.27 mmol) is added to a stirred mixture of 4-[(4-methyl-1-piperazinyl)-methyl]-N-{4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]-amino]-phenyl}-benzamide (prepared as described in EP 0 564 409 B1, Example 21; 2.00 g, 4.05 mmol) in dichloromethane (70 mL) at −20° C. The resulting mixture is then stirred at RT for 72 h. The solvent is then evaporated off under reduced pressure to yield a mixture which is purified by column chromatography on silica gel, eluent dichloromethane-methanol-water (70:30:5), to give the title compound as a yellow crystalline solid, m.p. 154-158° C.

Workup

  1. customThe solvent is then evaporated off under reduced pressure
  2. customto yield a mixture which
  3. customis purified by column chromatography on silica gel, eluent dichloromethane-methanol-water (70:30:5)

Sources & evidence

ORD record
ord-13ff01816f454af5af7a0de0a8b6e713
Source dataset
uspto-grants-2009_07
Patent number
US07557105B2

Reaction notes

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