Imatinib → Imatinib

HRID 1893732Notes

Reaction equation

HRID 1893732 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:37]=[CH:36][C:12]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([NH:23][C:24]4[N:29]=[C:28]([C:30]5[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=5)[CH:27]=[CH:26][N:25]=4)[CH:17]=3)=[O:14])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[C:38]1([S:44]([OH:47])(=[O:46])=[O:45])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C1(C)C=CC=CC=1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([NH:23][C:24]4[N:29]=[C:28]([C:30]5[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=5)[CH:27]=[CH:26][N:25]=4)[CH:17]=3)=[O:14])=[CH:36][CH:37]=2)[CH2:4][CH2:3]1.[C:38]1([S:44]([O-:47])(=[O:46])=[O:45])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 2

HCID 5291ImatinibHCID 7371Benzenesulfonic Acid

Product 2

HCID 5291ImatinibHCID 91526Benzenesulfonate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-[(4-Methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide (4.94 g, 10 mmol) is added to a solution of benzenesulphonic acid (Fluka, Buchs, Switzerland; 1.61 g, 10 mmol) in hot toluene (40 mL). The solution is evaporated to dryness under reduced pressure and the resulting residue is re-crystallized from ethanol-ethylacetate. The product is filtered-off and dried to afford 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide, benzenesulphonate as a pale-yellow crystalline solid, having the following analytical properties: Analysis found: C, 64.19; H, 5.68; N, 14.93; S, 4.87%; H2O, 0.34%. Calculated for C35H37N7O4S-0.12 H2O: C, 64.28; H, 5.74; N, 14.99; S, 4.90%; H2O, 0.33%.

Workup

  1. customThe solution is evaporated to dryness under reduced pressure
  2. customthe resulting residue is re-crystallized from ethanol-ethylacetate
  3. customdried

Sources & evidence

ORD record
ord-62bb0c24969843e3bc6c944bd45fa369
Source dataset
uspto-grants-2013_08
Patent number
US08513256B2

Reaction notes

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