Sodium Bicarbonate → HCID 9842936, Verbindung

HRID 1353015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1353015
CC1[N:3]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][CH:20]([C:22]([F:25])([F:24])[F:23])[N:19]=[C:18]3[C:26]3[C:27]([CH3:32])=[N:28][CH:29]=[CH:30][CH:31]=3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])C(C)=CC=1.C(=O)(O)[O-].[Na+]>C(O)(C(F)(F)F)=O.O>[CH3:32][C:27]1[C:26]([C:18]2[N:17]([C:14]3[CH:15]=[CH:16][C:11]([S:8]([NH2:3])(=[O:10])=[O:9])=[CH:12][CH:13]=3)[CH:21]=[C:20]([C:22]([F:23])([F:24])[F:25])[N:19]=2)=[CH:31][CH:30]=[CH:29][N:28]=1

Komponenten

5

Edukt 2

HCID 516892Sodium BicarbonateHCID 22997798HCID 22997798, Verbindung

Produkt 1

HCID 9842936HCID 9842936, VerbindungAusbeute 78,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A mixture of 3-[1-[4-[(2,5-dimethyl-1H-pyrrol-1-yl)sulfonyl]phenyl]-4,5-dihydro-4-(trifluoromethyl)-1H-imidazol-2-yl]-2-methylpyridine (Step 4) (4.6 g, 0.01 mol) in 75 mL of TFA and 25 mL of water was heated at reflux for 2 hours. The solution was cooled, treated with 400 nL of water and basified with sodium bicarbonate to pH 8. The aqueous phase was extracted with ethyl acetate (400 mL). The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated and the crude was purified by chromatography on silica gel (ethyl acetate/acetone, 95:5) to afford 4-[2-(2-methylpyridin-3-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide as a white solid (3.0 g, 78%): mp (DSC): 235–237° C. Anal. Calc'd. for C16H13F3N3O2S: C, 50.26; H, 3.43; N, 14.65; S, 8.39. Found: C, 50.06; H,3.29; N. 14.4; S, 8.52.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperatureThe solution was cooled
  4. extractionThe aqueous phase was extracted with ethyl acetate (400 mL)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customthe crude was purified by chromatography on silica gel (ethyl acetate/acetone, 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-0ef5eaee6e7041038c85e8575e775335
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07220770B2

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