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Hydrochloric Acid → 4-[4-(2-Fluoro-4-methanesulfonyl-phenoxy)pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid isopropyl ester

HRID 1931632
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1931632
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22]([O:23][C:24]4[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][C:25]=4[F:34])=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])(C)([CH3:3])[CH3:2].Cl.C(N(CC)CC)C.ClC(OC(C)C)=O>O1CCOCC1.O.C(OCC)(=O)C>[CH:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22]([O:23][C:24]4[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][C:25]=4[F:34])=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 44514402HCID 44514402, Verbindung

Produkt 1

HCID 445141094-[4-(2-Fluoro-4-methanesulfonyl-phenoxy)pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid isopropyl esterAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 4-[4-(2-fluoro-4-methanesulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (Example 60; 90 mg, 0.18 mmol) and 4 M HCl in dioxane (2 mL) was stirred at room temperature for 5 h. The solvent was evaporated and the residue was dried in vacuo to give a solid. To the solid were added ethyl acetate (3 mL) and triethylamine (74 mg, 0.73 mmol). The mixture was cooled to 10° C. and isopropyl chloroformate (1 M in toluene; 0.22 mL, 0.22 mmol) was added dropwise. The reaction mixture was allowed to warm to room temperature and stirred overnight. Water was added and the mixture was extracted with ethyl acetate. The combined organic layers were dried (sodium sulfate), filtered, evaporated, and purified by flash chromatography, eluting with 30% ethyl acetate/hexanes, to give 4-[4-(2-fluoro-4-methanesulfonyl-phenoxy)pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid isopropyl ester (30 mg, 35%) as an off-white solid. Mass spectrum (ES) MH+=478.

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue was dried in vacuo
  3. customto give a solid
  4. temperatureThe mixture was cooled to 10° C.
  5. temperatureto warm to room temperature
  6. stirringstirred overnight
  7. extractionthe mixture was extracted with ethyl acetate
  8. dry with materialThe combined organic layers were dried (sodium sulfate)
  9. filtrationfiltered
  10. customevaporated
  11. custompurified by flash chromatography
  12. washeluting with 30% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-dedcfa9904ad4cdb92f89aca3148196b
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08188098B2

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