Ethanol → Sunitinib acid

HRID 271544Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271544
[CH:1]([C:3]1[NH:7][C:6]([CH3:8])=[C:5]([C:9]([OH:11])=[O:10])[C:4]=1[CH3:12])=O.[F:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18](=[O:23])[CH2:17]2.C(O)C.N1CCCC1>C(O)(=O)C>[F:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18](=[O:23])/[C:17]/2=[CH:1]\[C:3]1[NH:7][C:6]([CH3:8])=[C:5]([C:9]([OH:11])=[O:10])[C:4]=1[CH3:12]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 31268PyrrolidineHCID 37310125-fluoro-1,3-dihydro-2H-indol-2-oneHCID 110737925-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic Acid

Produkt 1

HCID 10979489Sunitinib acidAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (61 g), 5-fluoro-1,3-dihydro-indol-2-one (79 g), ethanol (300 mL) and pyrrolidine (32 mL) were refluxed for 4.5 hours. Acetic acid (24 mL) was added to the mixture and refluxing was continued for 30 minutes. The mixture was cooled to room temperature and the solids collected by vacuum filtration and washed twice with ethanol. The solids were stirred for 130 minutes in 40% acetone in water (400 mL) containing 12 N hydrochloric acid (6.5 mL). The solids were collected by vacuum filtration and washed twice with 40% acetone in water. The solids were dried under vacuum to give 5-[5-fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (86 g, 79% yield) as an orange solid. 1H-NMR (dimethylsulfoxide-d6) δ 2.48, 2.50 (2×s, 6H, 2×CH3), 6.80, 6.88, 7.68, 7.72 (4×m, 4H, aromatic and vinyl), 10.88 (s, 1H, CONH), 12.12 (s, 1H, COOH), 13.82 (s, 1H, pyrrole NH). MS m/z 299 [M−1].

Aufarbeitung

  1. temperaturerefluxing
  2. filtrationthe solids collected by vacuum filtration
  3. washwashed twice with ethanol
  4. additioncontaining 12 N hydrochloric acid (6.5 mL)
  5. filtrationThe solids were collected by vacuum filtration
  6. washwashed twice with 40% acetone in water
  7. customThe solids were dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e968389287d04e8a9789e9c583102bea
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452913B2

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