L-Tartaric acid → HCID 86658827, compound

HRID 2360072Notes

Reaction equation

HRID 2360072 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 444305L-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 86658827HCID 86658827, compoundYield 61.5%

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 L-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 4.20 g of sunitinib L-tartarate. Melting point: 219-223° 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-05901a29b5d74be6990103927b487394
Source dataset
uspto-grants-2014_04
Patent number
US08686023B2

Reaction notes

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