Potassium Hydroxide → HCID 178494285, Verbindung

HRID 550850Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 550850
CS([C:5]1[N:6]=[C:7]([O:34][CH3:35])[C:8]2[N:13]=[C:12]([NH:14][C:15]([N:17]3[CH2:22][CH2:21][C:20]([OH:33])([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=4)[CH2:19][CH2:18]3)=[O:16])[S:11][C:9]=2[N:10]=1)(=O)=O.[OH-:36].[K+]>C1COCC1.O>[OH:36][C:5]1[N:6]=[C:7]([O:34][CH3:35])[C:8]2[N:13]=[C:12]([NH:14][C:15]([N:17]3[CH2:22][CH2:21][C:20]([OH:33])([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=4)[CH2:19][CH2:18]3)=[O:16])[S:11][C:9]=2[N:10]=1

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 248306134-Hydroxy-4-[3-(trifluoromethy)phenyl]piperidine-1-carboxylic acid (5-methanesulfonyl-7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide

Produkt 1

HCID 178494285HCID 178494285, VerbindungAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A magnetically stirred mixture of 4-hydroxy-4-[3-(trifluoromethy)phenyl]piperidine-1-carboxylic acid (5-methanesulfonyl-7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide (250 mg, 0.47 mmol) in THF (10 mL) and water (5 mL) was treated with a 2N aqueous KOH solution (0.5 mL, 0.94 mmol). The reaction mixture was stirred at 75° C. for 4 h. The reaction was then cooled to room temperature and poured into water and extracted with methylene chloride. The organics were washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated in vacuo to afford 4-hydroxy-4-[3-(trifluoromethy)phenyl]piperidine-1-carboxylic acid (5-hydroxy-7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide (32 mg, 15%) as a white solid. LRMS for C19H18F3N5O4S2 (M+H)+ at m/z=469. The NMR spectrum obtained on the sample is compatible with its structure.

Aufarbeitung

  1. temperatureThe reaction was then cooled to room temperature
  2. extractionextracted with methylene chloride
  3. washThe organics were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f6b31592a9ae435893220359cb726dbe
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947692B2

Notizen zur Reaktion

Wird geladen…