D-Tartaric acid → HCID 86658826, compound

HRID 2360075Notes

Reaction equation

HRID 2360075 reaction equation
[CH2:1]([N:3]([CH2:18][CH3:19])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[C:13]([CH3:14])=[C:12]([CH:15]=O)[NH:11][C:10]=1[CH3:17])=[O:8])[CH3:2].[F:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25](=[O:30])[CH2:24]2.[C:31]([OH:40])(=[O:39])[C@H:32]([C@@H:34]([C:36]([OH:38])=[O:37])[OH:35])[OH:33]>C(O)C.N1CCCC1>[CH3:2][CH2:1][N:3]([CH2:4][CH2:5][NH:6][C:7]([C:9]1[C:13]([CH3:14])=[C:12](/[CH:15]=[C:24]2/[C:23]3[CH:22]=[C:21]([F:20])[CH:29]=[CH:28][C:27]=3[NH:26][C:25]/2=[O:30])[NH:11][C:10]=1[CH3:17])=[O:8])[CH2:18][CH3:19].[C:31]([O-:40])(=[O:39])[C@H:32]([C@@H:34]([C:36]([O-:38])=[O:37])[OH:35])[OH:33]

Participants

6

Reactant 3

HCID 439655D-Tartaric acidHCID 37310125-fluoro-1,3-dihydro-2H-indol-2-oneHCID 20761785N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

Product 1

HCID 86658826HCID 86658826, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 31268PyrrolidineSolvent

Procedure

To a solution of 6.63 g (25 mmol) N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide (I) and 3.78 g (25 mmol) 5-fluoroindolin-2-one (II) in ethanol (400 ml), 0.25 ml of pyrrolidine was added and mixture was refluxed for 5 h. To a boiling reaction mixture, a solution of D-tartaric acid (1.88 g, 12.5 mmol) in ethanol (20 ml) was added and a solution was left to cool to room temperature, with slow (as slow as possible) stirring. The stirring was continued for another 16 hours, then the product was filtered to get 4.53 g of sunitinib D-tartarate. Melting point: 220-226° C. (Form III), ratio sunitinib/tartaric acid (according to NMR) 2:1.

Workup

  1. temperaturemixture was refluxed for 5 h
  2. customTo a boiling reaction mixture
  3. waita solution was left
  4. filtrationthe product was filtered

Sources & evidence

ORD record
ord-dd4ec216fede488782791268d4c0a7ea
Source dataset
uspto-grants-2014_04
Patent number
US08686023B2

Reaction notes

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