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Isopropanol → 2-(2-Methylpyrazolo[1,5-a]pyridin-3-yl)-4-(2-nitrophenyl)-1,3-thiazole-5-carboxylic acid

HRID 1530060
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1530060
Cl.[CH3:2][C:3]1[C:11]([C:12](=[S:14])[NH2:13])=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1.Cl[CH:16]([C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N+:30]([O-:32])=[O:31])=O)[C:17]([O:19]CC)=[O:18].CC(O)C.C(=O)(O)[O-].[Na+]>C1COCC1.CCOC(C)=O>[CH3:2][C:3]1[C:11]([C:12]2[S:14][C:16]([C:17]([OH:19])=[O:18])=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[N+:30]([O-:32])=[O:31])[N:13]=2)=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 3776IsopropanolHCID 516892Sodium BicarbonateHCID 866495852-Methylpyrazolo[1,5-a]pyridine-3-carbothioamide hydrochlorideHCID 86649598Ethyl 2-chloro-3-(2-nitrophenyl)-3-oxopropanoate

Produkt 1

HCID 668550542-(2-Methylpyrazolo[1,5-a]pyridin-3-yl)-4-(2-nitrophenyl)-1,3-thiazole-5-carboxylic acidAusbeute 31,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 2-methylpyrazolo[1,5-a]pyridine-3-carbothioamide hydrochloride (1.2 g, 5.2 mmol) obtained in Example 11-B(v), ethyl 2-chloro-3-(2-nitrophenyl)-3-oxopropanoate (1.7 g, 8.4 mmol) obtained above and 2-propanol (20 mL) was stirred at 80° C. for 4 h. To the reaction mixture were added saturated aqueous solution of sodium bicarbonate, EtOAc and THF. Insoluble materials were removed by filtration and the filtrate was extracted with a 1:1 mixture of EtOAc and THF. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. To the residue were added MeOH (10 mL), THF (25 mL) and 8N aqueous sodium hydroxide solution (2.5 mL), and the mixture was stirred at 70° C. for 1 h. The reaction mixture was allowed to, cool to 0° C., 6N hydrochloric acid was added to adjust the solution to about pH 3.0. The resulting precipitate was collected by filtration, washed with diisopropyl ether, and dried to give the title compound (620 mg, 31%) as a yellow solid.

Aufarbeitung

  1. customInsoluble materials were removed by filtration
  2. extractionthe filtrate was extracted with a 1:1 mixture of EtOAc and THF
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customInsoluble materials were removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. additionTo the residue were added MeOH (10 mL), THF (25 mL) and 8N aqueous sodium hydroxide solution (2.5 mL)
  8. stirringthe mixture was stirred at 70° C. for 1 h
  9. temperaturecool to 0° C.
  10. addition6N hydrochloric acid was added
  11. filtrationThe resulting precipitate was collected by filtration
  12. washwashed with diisopropyl ether
  13. customdried

Quellen und Nachweise

ORD-Eintrag
ord-773756b019b94b288b5d9e6536889927
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09090601B2

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