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N2-Methyl-5-(trifluoromethyl)pyridine-2,3-diamine → 5-{4-(3-Methyl-6-trifluoromethylimidazo[5,4-b]pyridin-2-ylmethoxy)benzyl}thiazolidine-2,4-dione

HRID 1599233
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Reaktionsgleichung

Reaktionsgleichung von HRID 1599233
O=[CH:2][CH2:3][O:4][C:5]1[CH:18]=[CH:17][C:8]([CH2:9][CH:10]2[S:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:7][CH:6]=1.[NH2:19][C:20]1[C:21]([NH:30][CH3:31])=[N:22][CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1>C(O)C.C(O)(=O)C>[CH3:31][N:30]1[C:21]2=[N:22][CH:23]=[C:24]([C:26]([F:29])([F:27])[F:28])[CH:25]=[C:20]2[N:19]=[C:2]1[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][CH:10]2[S:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:17][CH:18]=1
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Komponenten

5

Edukt 2

HCID 2735930N2-Methyl-5-(trifluoromethyl)pyridine-2,3-diamineHCID 108492775-[4-(2-Oxoethoxy)benzyl]thiazolidine-2,4-dione

Produkt 1

HCID 106705615-{4-(3-Methyl-6-trifluoromethylimidazo[5,4-b]pyridin-2-ylmethoxy)benzyl}thiazolidine-2,4-dioneAusbeute 7,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittel
HCID 702
Ethanol
Lösungsmittel

Versuchsvorschrift

4.16 g of 5-(4-(2-oxoethoxy)benzyl)thiazolidine-2,4-dione (prepared as described in Preparation 47) were added to a solution of 3.00 g of 3-amino-2-methylamino-5-trifluoromethylpyridine in a mixture of 6 ml of ethanol and 6 ml of acetic acid, and the resulting mixture was stirred at room temperature for 4 hours. At the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure. 50 ml of 1,2-dimethoxyethane and 5.2 g of iodine were added to the residue, and the resulting mixture was stirred at 60° C. for one day. At the end of this time, the reaction mixture was poured into water, after which it was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 1: 1 by volume mixture of hexane and ethyl acetate as the eluent. The product was crystallized by trituration with ethyl acetate, to give 520 mg of the title compound, melting at 212°-214° C.

Aufarbeitung

  1. distillationAt the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure
  2. addition50 ml of 1,2-dimethoxyethane and 5.2 g of iodine were added to the residue
  3. stirringthe resulting mixture was stirred at 60° C. for one day
  4. additionAt the end of this time, the reaction mixture was poured into water
  5. extractionafter which it was extracted with ethyl acetate
  6. washThe extract was washed with an aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. customafter which the solvent was removed by distillation under reduced pressure
  9. customThe residue was purified by column chromatography through silica gel
  10. additionby volume mixture of hexane and ethyl acetate as the eluent
  11. customThe product was crystallized by trituration with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-66b7feff89434bcca9171a3bed9541f3
Quelldatensatz
uspto-grants-1998_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05739345

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