L-Malic Acid → Sunitinib Malate

HRID 2192695Notes

Reaction equation

HRID 2192695 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]>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

4

Reactant 2

HCID 222656L-Malic AcidHCID 5329102Sunitinib

Product 1

HCID 6456015Sunitinib MalateYield 97.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of sunitinib free base (5.0 gm), L-malic acid (1.8 gm) and water (75 ml) was heated to 80 deg C. to obtain a clear solution, stirred for 30 minutes at 80 deg C. and slowly cooled to room temperature. The solution was subjected to freeze drying at about −90 deg C. for 7 hours to obtain 6.5 gm of sunitinib malate crystalline form III.

Workup

  1. temperaturewas heated to 80 deg C
  2. customto obtain a clear solution
  3. customto freeze drying at about −90 deg C

Sources & evidence

ORD record
ord-7f8aaca8ab3c4e00817a91ac245618e8
Source dataset
uspto-grants-2012_12
Patent number
US08329740B2

Reaction notes

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