Water → Imatinib

HRID 1893730Notes

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]([OH:45])(=[O:44])[CH2:39][CH2:40][C:41]([OH:43])=[O:42].O>C(O)C>[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]([O-:45])(=[O:44])[CH2:39][CH2:40][C:41]([O-:43])=[O:42]

Participants

Conditions

Temperature: 90 °C

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 butanedioic acid (succinic acid; Fluka, Buchs, Switzerland; 1.18 g, 10 mmol) is added to a solution of in ethanol (25 mL). The mixture is heated to 90° C., treated with water (0.2 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, succinate as a pale-yellow crystalline solid, having the following analytical properties: Analysis found: C, 64.19; H, 6.11; N, 15.82%; H2O, 0.87%. Calculated for C33H37N7O5-0.30 H2O: C, 64.23; H, 6.14; N, 15.89%; H2O, 0.88%.

Workup

filtrationfiltered
temperatureUpon cooling
customthe product crystallizes
filtrationis filtered
customdried

Sources & evidence

ORD record: ord-7a1b0576a56b47afa47ee4b1636dc416
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513256B2

Reaction notes

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