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Hydrochloric Acid → 4-(2,4-Difluorophenyl)-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxylic acid

HRID 2282248
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2282248
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([C:18]2[C:19]([CH3:27])=[N:20][N:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=23)[S:12][C:13]=1[C:14]([O:16]C)=[O:15].[OH-].[Na+].CCOC(C)=O.Cl>C1COCC1.CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([C:18]2[C:19]([CH3:27])=[N:20][N:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=23)[S:12][C:13]=1[C:14]([OH:16])=[O:15]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 66854887Methyl 4-(2,4-difluorophenyl)-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxylate

Produkt 1

HCID 668564524-(2,4-Difluorophenyl)-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxylic acidAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a suspension of methyl 4-(2,4-difluorophenyl)-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxylate (250 mg, 0.649 mmol) obtained above in THF (5 mL) and MeOH (5 mL), was added 2N aqueous solution of sodium hydroxide (1 mL) and the mixture was stirred for 2 h at 60° C. To the mixture, was added a 2:1 mixture of EtOAc and THF (60 mL) and 1N hydrochloric acid. The organic layer was separated and the aqueous layer was extracted with a 2:1 mixture of EtOAc and THF (10 mL). The combined organic layers were washed with brine (5 mL) and then dried over anhydrous sodium sulfate. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure to obtain title compound (225 mg, 93%) as a pale yellow solid.

Aufarbeitung

  1. additionTo the mixture, was added
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with a 2:1 mixture of EtOAc and THF (10 mL)
  4. washThe combined organic layers were washed with brine (5 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customInsoluble materials were removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ab43d2760e314fe7973d2d6d47a0038c
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09139589B2

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