Imatinib → Imatinib

HRID 1893728Notes

Reaction equation

HRID 1893728 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.[OH:38][C@@H:39]([CH2:43][C:44]([OH:46])=[O:45])[C:40]([OH:42])=[O:41]>O>[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:40]([O-:42])(=[O:41])[CH:39]([CH2:43][C:44]([O-:46])=[O:45])[OH:38]

Participants

5

Reactant 2

HCID 5291ImatinibHCID 222656L-Malic Acid

Product 2

HCID 5291ImatinibHCID 160434DL-Malate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 (2S)-(−)-hydroxybutanedioic acid (L-(−)-malic acid; Fluka, Buchs, Switzerland; 1.34 g, 10 mmol) in water (40 mL). The mixture is heated and the resulting hot solution is filtered and evaporated to dryness under reduced pressure to give a residue which is re-crystallized from ethanol, filtered and dried to give 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]benzamide, malate as a pale-yellow crystalline solid, having the following analytical properties: Analysis found: C, 62.88; H, 6.04; N, 15.60%; H2O, 0.45%. Calculated for C33H37N7O6-0.16 H2O: C, 62.86; H, 5.97; N, 15.55%; H2O, 0.46%.

Workup

  1. temperatureThe mixture is heated
  2. filtrationthe resulting hot solution is filtered
  3. customevaporated to dryness under reduced pressure
  4. customto give a residue which
  5. customis re-crystallized from ethanol
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-758433c44ae948e281f00687d70d5bc7
Source dataset
uspto-grants-2013_08
Patent number
US08513256B2

Reaction notes

Loading…