Water → Imatinib

HRID 1893729Notes

Reaction equation

HRID 1893729 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[CH3:9][N:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:45]=[CH:44][C:20]([C:21]([NH:23][C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([NH:31][C:32]4[N:37]=[C:36]([C:38]5[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=5)[CH:35]=[CH:34][N:33]=4)[CH:25]=3)=[O:22])=[CH:19][CH:18]=2)[CH2:12][CH2:11]1.O>C(O)C>[CH3:9][N:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:21]([NH:23][C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([NH:31][C:32]4[N:37]=[C:36]([C:38]5[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=5)[CH:35]=[CH:34][N:33]=4)[CH:25]=3)=[O:22])=[CH:44][CH:45]=2)[CH2:12][CH2:11]1.[C:1]([O-:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([O-:6])=[O:5]

Participants

6

Reactant 3

HCID 962WaterHCID 5291ImatinibHCID 444972Fumaric Acid

Product 2

HCID 5291ImatinibHCID 5460307Fumarate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

(Trans)-butenedioic acid (fumaric acid; Fluka, Buchs, Switzerland; 1.16 g, 10 mmol) is added to a solution of 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]benzamide (4.94 g, 10 mmol) in ethanol (25 mL). The mixture is heated to 90° C., treated with water (18 g) and filtered. Upon cooling, the product crystallizes and is filtered and dried to afford 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide, fumarate a pale-yellow crystalline solid, having the following analytical properties: Analysis found: C, 63.91; H, 5.99; N, 15.74%; H2O, 1.27%. Calculated for C33H35N7O5-0.44 H2O: C, 64.18; H, 5.86; N, 15.88%; H2O, 1.28%.

Workup

  1. filtrationfiltered
  2. temperatureUpon cooling
  3. customthe product crystallizes
  4. filtrationis filtered
  5. customdried

Sources & evidence

ORD record
ord-2307624645a84ec1a6c4bec28a5454ed
Source dataset
uspto-grants-2013_08
Patent number
US08513256B2

Reaction notes

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