4-Hydroxy-3,5-dimethoxycinnamic acid → Sunitinib sinapinate

HRID 1500393

Reaktionsgleichung

Reaktionsgleichung von HRID 1500393
[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:45])(=[O:44])/[CH:31]=[CH:32]/[C:33]1[CH:43]=[C:40]([O:41][CH3:42])[C:38]([OH:39])=[C:35]([O:36][CH3:37])[CH:34]=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].[CH3:42][O:41][C:40]1[CH:43]=[C:33](/[CH:32]=[CH:31]/[C:30]([OH:45])=[O:44])[CH:34]=[C:35]([O:36][CH3:37])[C:38]=1[OH:39]

Komponenten

4

Edukt 2

HCID 6377754-Hydroxy-3,5-dimethoxycinnamic acidHCID 5329102Sunitinib

Produkt 1

HCID 131734271Sunitinib sinapinateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

Sunitinib (1.0 g) was suspended in methanol (152 mL), followed by addition of sinapic acid (0.56 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 sinapinate.(1.3 g; yield:83%)

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4dd023a3295c48b19afb6d1b4770a45e
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206163B2

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