Malic Acid → Sunitinib Malate

HRID 1918253Notes

Reaction equation

HRID 1918253 reaction equation
[CH3:1][CH2:2][N:3]([CH2:6][CH2:7][NH:8][C:9]([C:11]1[C:15]([CH3:16])=[C:14](/[CH:17]=[C:18]2/[C:19]3[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=3[NH:26][C:27]/2=[O:28])[NH:13][C:12]=1[CH3:29])=[O:10])[CH2:4][CH3:5].[C:30]([OH:38])(=[O:37])[CH:31]([CH2:33][C:34]([OH:36])=[O:35])[OH:32].C(OCC)(=O)C>CS(C)=O>[CH3:1][CH2:2][N:3]([CH2:6][CH2:7][NH:8][C:9]([C:11]1[C:15]([CH3:16])=[C:14](/[CH:17]=[C:18]2/[C:19]3[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=3[NH:26][C:27]/2=[O:28])[NH:13][C:12]=1[CH3:29])=[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 525Malic AcidHCID 8857Ethyl AcetateHCID 5329102Sunitinib

Product 1

HCID 6456015Sunitinib MalateYield 77.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1 g of sunitinib base was suspended in 4 ml of DMSO, at RT. 0.336 g of Malic acid added (as a solid) obtaining a solution, then 20 ml of ethyl acetate were added drop wise and precipitation was observed. The suspension was kept at 20-25° C. for 1 hour then filtered and washed with ethyl acetate. Dried at 80° C. under vacuum for 16-18 h affording 1.03 g of Sunitinib Malate.

Workup

  1. customobtaining a solution
  2. customprecipitation
  3. filtrationthen filtered
  4. washwashed with ethyl acetate
  5. customDried at 80° C. under vacuum for 16-18 h

Sources & evidence

ORD record
ord-38b797fd3e494780abccc99086bdc99c
Source dataset
uspto-grants-2013_12
Patent number
US08618309B2

Reaction notes

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