Isopropyl Acetate → Sunitinib Malate

HRID 2192698Notes

Reaction equation

HRID 2192698 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 74.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sunitinib free base (5.0 gm) and L-malic acid (1.8 gm) was added to dimethyl sulfoxide (25 ml), and the mixture was heated to 80 deg C. to obtain a clear solution, stirred for 30 minutes at 80 deg C. Isopropyl acetate (120 ml) was added to the solution at 80 deg C. and stirred for 2 hours at 80 deg C. The solution was slowly cooled to room temperature and stirred for 1 hour at room temperature. The contents are filtered and the solid obtained was washed with isopropyl acetate (15 ml), and then dried the solid at 60 deg C. under vacuum to obtain 5.0 gm of sunitinib malate crystal form I.

Workup

  1. temperaturethe mixture was heated to 80 deg C
  2. customto obtain a clear solution
  3. stirringand stirred for 2 hours at 80 deg C
  4. stirringstirred for 1 hour at room temperature
  5. filtrationThe contents are filtered
  6. customthe solid obtained
  7. washwas washed with isopropyl acetate (15 ml)
  8. customdried the solid at 60 deg C

Sources & evidence

ORD record
ord-9387965b89894393ad2411143e782ace
Source dataset
uspto-grants-2012_12
Patent number
US08329740B2

Reaction notes

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