L-Malic Acid → HCID 131734267, compound

HRID 1500388Notes

Reaction equation

HRID 1500388 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]>CO>[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]([O-:38])(=[O:37])[C@H:31]([CH2:33][C:34]([O-:36])=[O:35])[OH:32]

Participants

4

Reactant 2

HCID 222656L-Malic AcidHCID 5329102Sunitinib

Product 1

HCID 131734267HCID 131734267, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
27.5 °C

Procedure

Sunitinib (10 g) was suspended in methanol (1540 mL) under stirring and L-malic acid (3.36 g) was added to it at a temperature 25-30° C. The reaction mass was stirred to get a clear solution. It was filtered and methanol was distilled off under vacuum below 40° C. Acetonitrile (50 mL) was charged and the solvent was distilled off. It was cooled to 25-30° C. 380 mL of acetonitrile was added to the mass and it was mentained at 45-50° C. under stirring for a period of 15 minutes. The reaction mass was cooled to 30-35° C. The solid obtained was filtered and washed with acetonitrile (10 mL). The resultant compound was suck dried and dried under vacuum over a period of 4-5 hrs at 50° C. to obtain sunitinib L-malate. (12.0 g; yield 90%)

Workup

  1. stirringThe reaction mass was stirred
  2. customto get a clear solution
  3. filtrationIt was filtered
  4. distillationmethanol was distilled off under vacuum below 40° C
  5. additionAcetonitrile (50 mL) was charged
  6. distillationthe solvent was distilled off
  7. addition380 mL of acetonitrile was added to the mass and it
  8. customwas mentained at 45-50° C.
  9. stirringunder stirring for a period of 15 minutes
  10. temperatureThe reaction mass was cooled to 30-35° C
  11. customThe solid obtained
  12. filtrationwas filtered
  13. washwashed with acetonitrile (10 mL)
  14. customdried
  15. customdried under vacuum over a period of 4-5 hrs at 50° C.

Sources & evidence

ORD record
ord-7d79ffbe420f4272addb3286f253a146
Source dataset
uspto-grants-2015_12
Patent number
US09206163B2

Reaction notes

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