Hydrochloric Acid → HCID 67486992, Verbindung

HRID 1809629Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1809629
C([O:4][CH2:5][C:6]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][CH:11]([C:16]1[N:20]=[C:19]([NH:21][C:22]3[C:27]([O:28][C:29]4[C:30]([CH3:35])=[N:31][CH:32]=[CH:33][CH:34]=4)=[CH:26][C:25]([S:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=4)=[CH:24][N:23]=3)[S:18][N:17]=1)[CH2:12]2)=[O:7])(=O)C.C([O-])([O-])=O.[K+].[K+].[ClH:49]>CCO>[ClH:49].[OH:4][CH2:5][C:6]([N:8]1[CH:9]2[CH2:15][CH2:14][CH:13]1[CH2:12][CH:11]([C:16]1[N:20]=[C:19]([NH:21][C:22]3[C:27]([O:28][C:29]4[C:30]([CH3:35])=[N:31][CH:32]=[CH:33][CH:34]=4)=[CH:26][C:25]([S:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=4)=[CH:24][N:23]=3)[S:18][N:17]=1)[CH2:10]2)=[O:7]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 67487819HCID 67487819, Verbindung

Produkt 1

HCID 67486992HCID 67486992, VerbindungAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

2-(3-(5-(3-(2-Methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octan-8-yl)-2-oxoethyl acetate (95 mg, 0.157 mmol) was dissolved in EtOH (3 mL) and K2CO3 (excess) was added and heated to 50° C. for 1.5 hr. The reaction was partitioned between CH2Cl2 and saturated aqueous NH4Cl, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel (15% methanol in EtOAc) to afford 2-hydroxy-1-(3-(5-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octan-8-yl)ethanone hydrochloride (78.2 mg, 0.131 mmol, 83.1% yield) as a solid after HCl salt formation. Mass spectrum (apci) m/z=562.2 (M+H—HCl).

Aufarbeitung

  1. customThe reaction was partitioned between CH2Cl2 and saturated aqueous NH4Cl
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel (15% methanol in EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-c829149fdb044caaa6f814f3800a3e12
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362037B2

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