Triethylamine → HCID 53628651, Verbindung

HRID 1260224

Reaktionsgleichung

Reaktionsgleichung von HRID 1260224
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C@@H:20]3[CH2:24][CH2:23][NH:22][CH2:21]3)=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[F:25][CH2:26][CH2:27][CH2:28]OS(C1C=CC(C)=CC=1)(=O)=O.C(N(CC)CC)C>CN(C)C=O>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C@@H:20]3[CH2:24][CH2:23][N:22]([CH2:28][CH2:27][CH2:26][F:25])[CH2:21]3)=[CH:16][CH:15]=2)(=[O:11])=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 8471Triethylamine2×HCID 63667743-Fluoroprop-1-yl toluene-4-sulphonate2×HCID 57470074HCID 57470074, Verbindung

Produkt 1

HCID 53628651HCID 53628651, VerbindungAusbeute 45,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

0.215 g of 4-isopropyl-N-[4-((S)-pyrrolidin-3-yl)-phenyl]-benzenesulfonamide (0.0.62 mmol) and 0.16 g of toluene-4-sulfonic acid 3-fluoro-propyl ester (0.69 mmol) were dissolved in 5 ml of dimethylformamide, 0.43 ml of triethylamine added and the reaction stirred for 1 h at 50° C. Additional toluene-4-sulfonic acid 3-fluoro-propyl ester and triethylamine were added to drive the reaction to completion. After stirring at room temperature for 15 h, the solvent was evaporated, the residue re-dissolved in dichloromethane, and the organic layer washed with 1 N aqueous sodium hydroxide. The aqueous phase was extracted twice with dichloromethane, the organic layers combined, dried over magnesium sulfate, filtered and the solvent evaporated. The crude product was purified via silica gel chromatography (chromabond column) using dichloromethane/methanol 0-3%. Fractions containing the product were collected and the solvent evaporated to yield 0.115 g of the desired product.

Aufarbeitung

  1. customthe reaction to completion
  2. stirringAfter stirring at room temperature for 15 h
  3. customthe solvent was evaporated
  4. dissolutionthe residue re-dissolved in dichloromethane
  5. washthe organic layer washed with 1 N aqueous sodium hydroxide
  6. extractionThe aqueous phase was extracted twice with dichloromethane
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. customThe crude product was purified via silica gel chromatography (chromabond column)
  11. additionFractions containing the product
  12. customwere collected
  13. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-74d3f94dd9534cc8bfd966331565caa9
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470810B2

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