Fumaric Acid → HCID 131734273, compound

HRID 1500396Notes

Reaction equation

HRID 1500396 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:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34]>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-:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([O-:35])=[O:34]

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 5329102Sunitinib

Product 1

HCID 131734273HCID 131734273, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

Sunitinib (1.0g) was suspended in methanol (152 mL), followed by addition of fumaric acid (0.29 g) at 25-35° C. over a period of 15 minutes. After the stipulated time period, methanol was completely distilled off under vacuum below 45° C. The residue was treated with acetonitrile (38 mL) and refluxed. The reaction mass was maintained at reflux temperature for 60 minutes. The reaction mass was cooled to 25-35° C. for crystallization. The solid obtained was filtered, washed with acetonitrile, suck dried and dried under vacuum at 60° C. over 4-5 hr period to obtain sunitinib fumarate.(1.2 g; yield: 93%)

Workup

  1. distillationAfter the stipulated time period, methanol was completely distilled off under vacuum below 45° C
  2. additionThe residue was treated with acetonitrile (38 mL)
  3. temperaturerefluxed
  4. temperatureThe reaction mass was maintained
  5. temperatureat reflux temperature for 60 minutes
  6. customThe solid obtained
  7. filtrationwas filtered
  8. washwashed with acetonitrile, suck
  9. customdried
  10. customdried under vacuum at 60° C. over 4-5 hr period

Sources & evidence

ORD record
ord-6838251f9f2b47d2875128febec9e17a
Source dataset
uspto-grants-2015_12
Patent number
US09206163B2

Reaction notes

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