2-Chloromandelic acid → Nilotinib 2-chloromandelate

HRID 1428270Notes

Reaction equation

HRID 1428270 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.[Cl:40][C:41]1[CH:51]=[CH:50][CH:49]=[CH:48][C:42]=1[CH:43]([OH:47])[C:44]([OH:46])=[O:45]>>[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.[Cl:40][C:41]1[CH:51]=[CH:50][CH:49]=[CH:48][C:42]=1[CH:43]([OH:47])[C:44]([O-:46])=[O:45]

Participants

3

Reactant 2

HCID 977202-Chloromandelic acidHCID 644241Nilotinib

Product 1

HCID 131732356Nilotinib 2-chloromandelate

Conditions

Temperature
5 °C

Procedure

Nilotinib base (0.300 g, 0.57 mmol) was dissolved in TFE (2 mL) at 40° C. to obtain a mixture. The mixture was stirred and added to a solution of 2-chloromandelic acid (0.106 g, 0.57 mmol) in TFE (1 mL) at 40° C. Stirring of the resulting solution was continued for about 1 h and it was subsequently cooled to 5° C. The mixture was kept at 5° C. overnight and then a sample (1 ml) was taken from the mixture and evaporated to dryness under reduced pressure at 40° C. to give amorphous Nilotinib 2-chloromandelate.

Workup

  1. customto obtain a mixture
  2. stirringStirring of the resulting solution
  3. waitThe mixture was kept at 5° C. overnight
  4. customevaporated to dryness under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-9a1ab83ba20b43a1bf9ef144ff505856
Source dataset
uspto-grants-2015_01
Patent number
US08937082B2

Reaction notes

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