1-Propanol → HCID 86619644, compound

HRID 1010816Notes

Reaction equation

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

Participants

Conditions

Temperature: 82 °C

Procedure

Imatinib base (3 g) was added to the solution of n-propanol (30 ml) and acetic acid (0.5 ml). The suspension was heated under reflux (82° C.) for 15 min providing thus a clear solution of imatinib acetate. Methanesulfonic acid (375 μl) was added providing the replacement of week acetic acid by stronger methanesulfonic acid and the volume of solution was reduced to ½ by evaporation at the vacuum evaporator at 20 mBar. Seeds of imatinib mesylate Form α were added (20 mg) and the solution was allowed to crystallize overnight. Crystals of imatinib mesylate Form a were recovered by filtration, washed with n-propanol, n-hexane and dried at 80° C. in a stream of nitrogen. Yield 2.97 g (83%).

Workup

temperatureThe suspension was heated

Sources & evidence

ORD record: ord-e520ae9a0d9b4c1ebc012803688360a2
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977348B2

Reaction notes

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