L-Tartaric acid → Nilotinib L-tartrate

HRID 1428276Notes

Reaction equation

HRID 1428276 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:49])(=[O:48])[C@@H:41]([C@H:43]([C:45]([OH:47])=[O:46])[OH:44])[OH:42]>>[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:45]([C@@H:43]([C@H:41]([C:40]([O-:49])=[O:48])[OH:42])[OH:44])([O-:47])=[O:46]

Participants

3

Reactant 2

HCID 444305L-Tartaric acidHCID 644241Nilotinib

Product 1

HCID 86688187Nilotinib L-tartrate

Conditions

Temperature
40 °C

Procedure

Nilotinib base (0.300 g, 0.57 mmol) was dissolved in TFE (2 mL) at 40° C. The stirred mixture was added to a solution of L-tartaric acid (0.083 g, 0.57 mmol) in TFE (1 mL) at 40° C. The resulting clear solution was stirred for about 4 h at 40° C. and subsequently cooled to 5° C. and kept at this temperature overnight leading to precipitation. The precipitate was filtered and the filter cake was dried at 40° C. in a vacuum oven overnight to give to give Nilotinib L-tartrate form II.

Workup

  1. temperaturesubsequently cooled to 5° C.
  2. customkept at this temperature overnight
  3. customleading to precipitation
  4. filtrationThe precipitate was filtered
  5. customthe filter cake was dried at 40° C. in a vacuum oven overnight
  6. customto give

Sources & evidence

ORD record
ord-00a8a4649906477f94059ffbb3d496a9
Source dataset
uspto-grants-2015_01
Patent number
US08937082B2

Reaction notes

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