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Cesium carbonate → 2-(4-{2-[2-(3,5-dimethoxyphenyl)ethyl]-5H-pyrrolo[2,3-b]pyrazin-6-yl}-1H-pyrazol-1-yl)ethanol

HRID 1052261
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1052261
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]2[N:14]=[C:15]3[CH:21]=[C:20]([C:22]4[CH:23]=[N:24][NH:25][CH:26]=4)[N:19](S(C4C=CC=CC=4)(=O)=O)[C:16]3=[N:17][CH:18]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:43][CH2:44][O:45][Si](C(C)(C)C)(C)C.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([CH2:11][CH2:12][C:13]2[N:14]=[C:15]3[CH:21]=[C:20]([C:22]4[CH:26]=[N:25][N:24]([CH2:43][CH2:44][OH:45])[CH:23]=4)[NH:19][C:16]3=[N:17][CH:18]=2)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 89963624HCID 89963624, Verbindung

Produkt 1

HCID 730565342-(4-{2-[2-(3,5-dimethoxyphenyl)ethyl]-5H-pyrrolo[2,3-b]pyrazin-6-yl}-1H-pyrazol-1-yl)ethanolAusbeute 14,5 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred solution of 2-[2-(3,5-dimethoxyphenyl)ethyl]-5-(phenylsulfonyl)-6-(1H-pyrazol-4-yl)-5H-pyrrolo[2,3-b]pyrazine (from Example 35, Step 1, 30.0 mg, 0.0613 mmol) in acetonitrile (1 mL), cesium carbonate (20.0 mg, 0.0613 mmol) and (2-bromoethoxy) (tert-butyl)dimethylsilane (13.1 μL, 0.0613 mmol) were added sequentially at ambient temperature. The reaction mixture was then warmed up to 60° C. After 2 hours, the reaction was quenched with water, and extracted with methylene chloride. The combined organic layers were dried over MgSO4, concentrated. The residue was dissolved in methylene chloride (1.0 m)/trifluoroacetic acid (1.0 mL) at ambient temperature. After 2 hours, the volatiles were removed under vacuum and the residues were dissolved in methanol (2.0 mL). Potassium carbonate (16.9 mg, 0.122 mmol) was added and the reaction mixture was warmed up to 60° C. After 1 hour, the crude mixture was purified on RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.05% TFA, at flow rate of 30 mL/min) to give the desired product (3.5 mg) as its TFA salt. LCMS calculated for C21H24N5O3 (M+H)+: m/z=394.2. Found: 394.2.

Aufarbeitung

  1. customthe reaction was quenched with water
  2. extractionextracted with methylene chloride
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in methylene chloride (1.0 m)/trifluoroacetic acid (1.0 mL) at ambient temperature
  6. waitAfter 2 hours
  7. customthe volatiles were removed under vacuum
  8. dissolutionthe residues were dissolved in methanol (2.0 mL)
  9. temperaturethe reaction mixture was warmed up to 60° C
  10. waitAfter 1 hour
  11. customthe crude mixture was purified on RP-HPLC (XBridge C18 column
  12. washeluting with a gradient of acetonitrile/water containing 0.05% TFA, at flow rate of 30 mL/min)

Quellen und Nachweise

ORD-Eintrag
ord-b00cad1138c64ada99502ed08e4bf668
Quelldatensatz
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09388185B2

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