Isopropyl Acetate → Sunitinib Malate

HRID 2192699Notes

Reaction equation

HRID 2192699 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].C(OC(C)C)(=O)C>CS(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 7915Isopropyl AcetateHCID 222656L-Malic AcidHCID 5329102Sunitinib

Product 1

HCID 6456015Sunitinib MalateYield 64.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

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 slowly cooled to room temperature and the solution was added to isopropyl acetate (72 ml). The solution was stirred for 2 hours at room temperature and filtered. The solid obtained was washed with mixture of dimethyl sulfoxide (1 ml) and isopropyl acetate (4 ml) and dried at 60 deg C. under vacuum to obtain 4.3 gm of sunitinib malate crystal form I.

Workup

  1. temperaturewas heated to 80 deg C
  2. customto obtain a clear solution
  3. stirringThe solution was stirred for 2 hours at room temperature
  4. filtrationfiltered
  5. customThe solid obtained
  6. washwas washed with mixture of dimethyl sulfoxide (1 ml) and isopropyl acetate (4 ml)
  7. customdried at 60 deg C

Sources & evidence

ORD record
ord-95f90dd1d75d4693a9adbb632b389896
Source dataset
uspto-grants-2012_12
Patent number
US08329740B2

Reaction notes

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