P-Coumaric Acid → HCID 178464064, compound

HRID 1500392Notes

Reaction equation

HRID 1500392 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].[CH:30]1[C:35](/[CH:36]=[CH:37]/[C:38]([OH:40])=[O:39])=[CH:34][CH:33]=[C:32]([OH:41])[CH:31]=1>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:38]([O-:40])(=[O:39])/[CH:37]=[CH:36]/[C:35]1[CH:34]=[CH:33][C:32]([OH:41])=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 637542P-Coumaric AcidHCID 5329102Sunitinib

Product 1

HCID 178464064HCID 178464064, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

Sunitinib (1.0 g) was suspended in methanol (152 mL), followed by addition of coumaric acid (0.41 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 coumarate.(1.1 g; yield:78%)

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-f2c9e8c836c7433296588558376da05f
Source dataset
uspto-grants-2015_12
Patent number
US09206163B2

Reaction notes

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