Sodium Hydroxide → Sunitinib

HRID 84785

Reaction equation

HRID 84785 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].CS([O-])(=O)=O.[OH-].[Na+]>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]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86691059Sunitinib methanesulfonate

Product 1

HCID 5329102SunitinibYield 99.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Sunitinib methanesulfonate (1.0 g) and H2O (60 mL) was added into a flask in r.t. and heated to 80° C., the mixture turned clear. The pH of the mixture was adjusted to 8˜9 with 1N NaOH and cooled r.t., was stirred overnight, filtered, washed, and dried in vacuo to give 0.65 g of crude sunitinib with 99.2% purity by HPLC analysis in 99.5% yield.

Workup

  1. temperaturecooled r.t.
  2. filtrationfiltered
  3. washwashed
  4. customdried in vacuo

Sources & evidence

ORD record
ord-b24cd80ef32e41859a7e5c7bd4853404
Source dataset
uspto-grants-2014_09
Patent number
US08846953B2

Linked notes

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