Dimethyl Sulfoxide → Sunitinib Malate

HRID 2192696Notes

Reaction equation

HRID 2192696 reaction equation
[CH3:1][CH2:2][N:3]([CH2:6][CH2:7][NH:8][C:9]([C:11]1[C:12]([CH3:29])=[C:13](/[CH:17]=[C:18]2/[C:19]3[CH:20]=[C:21]([F:28])[CH:22]=[CH:23][C:24]=3[NH:25][C:26]/2=[O:27])[NH:14][C:15]=1[CH3:16])=[O:10])[CH2:4][CH3:5].[C:30]([OH:38])(=[O:37])[C@H:31]([CH2:33][C:34]([OH:36])=[O:35])[OH:32].CS(C)=O>CC(C)=O>[CH3:1][CH2:2][N:3]([CH2:6][CH2:7][NH:8][C:9]([C:11]1[C:12]([CH3:29])=[C:13](/[CH:17]=[C:18]2/[C:19]3[CH:20]=[C:21]([F:28])[CH:22]=[CH:23][C:24]=3[NH:25][C:26]/2=[O:27])[NH:14][C:15]=1[CH3:16])=[O:10])[CH2:4][CH3:5].[CH2:33]([C:34]([OH:36])=[O:35])[C@H:31]([OH:32])[C:30]([OH:38])=[O:37]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 222656L-Malic AcidHCID 5329102Sunitinib

Product 1

HCID 6456015Sunitinib MalateYield 77.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The mixture of sunitinib free base (5.0 gm), L-malic acid (1.8 gm) and dimethyl sulfoxide (25 ml) was heated to 80 deg C. to obtain a clear solution, stirred for 30 minutes at 80 deg C. The solution was cooled to 55-60 deg C. and acetone (150 ml) was added to the solution at 55-60 deg C., stirred for 2 hours at 55-60 deg C. The solution was further cooled to room temperature, stirred for 1 hour at room temperature and filtered. The solid obtained was washed with acetone (15 ml) and dried the solid at 60 deg C. under vacuum to obtain 5.2 gm of sunitinib malate crystal form I

Workup

  1. temperaturewas heated to 80 deg C
  2. customto obtain a clear solution
  3. temperatureThe solution was cooled to 55-60 deg C
  4. stirring, stirred for 2 hours at 55-60 deg C
  5. stirringstirred for 1 hour at room temperature
  6. filtrationfiltered
  7. customThe solid obtained
  8. washwas washed with acetone (15 ml)
  9. customdried the solid at 60 deg C

Sources & evidence

ORD record
ord-5af5e6690b654ab09b634898c169bb29
Source dataset
uspto-grants-2012_12
Patent number
US08329740B2

Reaction notes

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