Imatinib → Imatinib

HRID 1893734Notes

Reaction equation

HRID 1893734 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][CH3:12].[CH3:13][N:14]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:49]=[CH:48][C:24]([C:25]([NH:27][C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([NH:35][C:36]4[N:41]=[C:40]([C:42]5[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=5)[CH:39]=[CH:38][N:37]=4)[CH:29]=3)=[O:26])=[CH:23][CH:22]=2)[CH2:16][CH2:15]1>C(O)C>[CH3:13][N:14]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:25]([NH:27][C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([NH:35][C:36]4[N:41]=[C:40]([C:42]5[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=5)[CH:39]=[CH:38][N:37]=4)[CH:29]=3)=[O:26])=[CH:48][CH:49]=2)[CH2:16][CH2:15]1.[C:6]([O-:8])(=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[C:3]([O:11][CH3:12])[CH:4]=1

Participants

5

Reactant 2

HCID 5291ImatinibHCID 8468Vanillic Acid

Product 2

HCID 5291ImatinibHCID 178492743HCID 178492743, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 4-hydroxy-3-methoxybenzoic acid (vanillic acid; Fluka, Buchs, Switzerland; 694 mg, 4 mmol) in ethanol (50 mL) is added to a solution of 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide (1.975 g, 4 mmol) in hot ethanol (150 mL at 90° C.). The solution is evaporated to dryness under reduced pressure and the resulting residue is re-crystallized from ethanol-acetone. 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, vanillate as a crystalline solid, having the following analytical properties: Analysis found: C, 66.61; H, 6.18; N, 14.74; 0, 12.86%. H2O, 0.84%. Calculated for C37H39N7O5-0.31 H2O: C, 66.59; H, 5.98; N, 14.69; O, 12.73%. H2O, 0.84%.

Workup

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

Sources & evidence

ORD record
ord-84789921a9214217a8e5871571e2c809
Source dataset
uspto-grants-2013_08
Patent number
US08513256B2

Reaction notes

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