Succinic Acid → Nilotinib succinate

HRID 1528231Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:21]([NH:23][C:24]2[CH:25]=[C:26]([C:36]([F:39])([F:38])[F:37])[CH:27]=[C:28]([N:30]3[CH:34]=[N:33][C:32]([CH3:35])=[CH:31]3)[CH:29]=2)=[O:22])=[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:40]([OH:47])(=[O:46])[CH2:41][CH2:42][C:43]([OH:45])=[O:44]>CN1C(=O)CCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:21]([NH:23][C:24]2[CH:25]=[C:26]([C:36]([F:38])([F:39])[F:37])[CH:27]=[C:28]([N:30]3[CH:34]=[N:33][C:32]([CH3:35])=[CH:31]3)[CH:29]=2)=[O:22])=[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:40]([O-:47])(=[O:46])[CH2:41][CH2:42][C:43]([O-:45])=[O:44]

Participants

Conditions

Temperature: 80 °C

Procedure

Nilotinib base (0.5 g, 0.94 mmol) and succinic acid (0.144 g, 0.94 mmol) were mixed with NMP (1.5 mL, 3.0V). The mixture was stirred and heated to 80° C. to dissolution. The stirring was continued at the same temperature for 5 h, after which the mixture was allowed to cool to room temperature resulting in precipitation. The precipitate was separated by filtration to give Nilotinib succinate form III. The filter cake was then washed with EtOH (27 mL, 95%) and dried in a vacuum oven (30 mbar) at 40° C. for 16 h to give Nilotinib succinate form III (0.17 g) as an off-white solid.

Workup

temperatureto cool to room temperature
customresulting in precipitation
customThe precipitate was separated by filtration

Sources & evidence

ORD record: ord-0aa29bd7f33f4e3a9303341d9451bbf8
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090598B2

Reaction notes

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