Thiazolidinedione → 3-[(6-Fluoro-3-{[4-(4-morpholinylmethyl)-1H-pyrrol-2-yl]methylene}-2-oxo-2,3-dihydro-1H-indol-5-yl)methyl]-1,3-thiazolidine-2,4-dione

HRID 1094021

Reaktionsgleichung

Reaktionsgleichung von HRID 1094021
[S:1]1[CH2:5][C:4](=[O:6])[NH:3][C:2]1=[O:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[F:43][C:44]1[CH:52]=[C:51]2[C:47]([C:48](=[CH:54][C:55]3[NH:56][CH:57]=[C:58]([CH2:60][N:61]4[CH2:66][CH2:65][O:64][CH2:63][CH2:62]4)[CH:59]=3)[C:49](=[O:53])[NH:50]2)=[CH:46][C:45]=1[CH2:67]O.N(C(OC(C)(C)C)=O)=NC([O-])=O>C1COCC1.CC#N>[F:43][C:44]1[CH:52]=[C:51]2[C:47]([C:48](=[CH:54][C:55]3[NH:56][CH:57]=[C:58]([CH2:60][N:61]4[CH2:62][CH2:63][O:64][CH2:65][CH2:66]4)[CH:59]=3)[C:49](=[O:53])[NH:50]2)=[CH:46][C:45]=1[CH2:67][N:3]1[C:4](=[O:6])[CH2:5][S:1][C:2]1=[O:7]

Komponenten

8

Edukt 5

HCID 5437Thiazolidinedione2×HCID 11776Triphenylphosphine2×HCID 97268Di-tert-butyl azodicarboxylateHCID 666364736-Fluoro-5-(hydroxymethyl)-3-{[4-(4-morpholinylmethyl)-1H-pyrrol-2-yl]methylene}-1,3-dihydro-2H-indol-2-oneHCID 86609045Tert-butyl azodicarboxylate

Produkt 1

HCID 866624343-[(6-Fluoro-3-{[4-(4-morpholinylmethyl)-1H-pyrrol-2-yl]methylene}-2-oxo-2,3-dihydro-1H-indol-5-yl)methyl]-1,3-thiazolidine-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Thiazolidine-2,4-dione (0.350 mmol) and triphenylphosphine on resin (1.66 mmol/g, 0.415 mmol) are stirred for 10 min. at ambient temperature in anhydrous THF (9 ml) under nitrogen. The mixture is cooled in an ice bath and di-tert-butyl azodicarboxylate (0.369 mmol) is added all at once. The mixture is stirred at 0° C. for 10 min, and then the compound obtained in Step D (0.238 mmol) is added all at once. The mixture is stirred at 0° C. for 1.5 hours, and then thiazolidine-2,4-dione (0.350 mmol), three portions of triphenylphosphine on resin (1.66 mmol/g; 0.166 mmol, 0.415 mmol and 0.166 mmol) and three portions of tert-butyl azodicarboxylate (each portion 0.369 mmol) are added over a period of 48 hours. Silica gel is added and the mixture is evaporated in vacuo. The residue obtained is purified by flash chromatography (DCM/MeOH 100:0 to 95:5) to yield a dark yellow solid which, after trituration in CH3CN, yields the title product in the form of a yellow solid.

Aufarbeitung

  1. temperatureThe mixture is cooled in an ice bath
  2. stirringThe mixture is stirred at 0° C. for 1.5 hours
  3. additionSilica gel is added
  4. customthe mixture is evaporated in vacuo
  5. customThe residue obtained
  6. customis purified by flash chromatography (DCM/MeOH 100:0 to 95:5)
  7. customto yield a dark yellow solid which

Quellen und Nachweise

ORD-Eintrag
ord-8cd2eea1f9504fad95fb35bf6b7e184d
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08133889B2

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