5-{2-[6-Methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-thiazol-4-yl}-thiophene-2-sulfonic acid tert-butylamide → 5-{2-[6-Methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-thiazol-4-yl}-thiophene-2-sulfonic acid amide

HRID 1928353Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1928353
C([NH:5][S:6]([C:9]1[S:10][C:11]([C:14]2[N:15]=[C:16]([C:19]3[CH:24]=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=4)[CH:22]=[C:21]([CH3:35])[N:20]=3)[S:17][CH:18]=2)=[CH:12][CH:13]=1)(=[O:8])=[O:7])(C)(C)C>C(O)(C(F)(F)F)=O>[CH3:35][C:21]1[N:20]=[C:19]([C:16]2[S:17][CH:18]=[C:14]([C:11]3[S:10][C:9]([S:6]([NH2:5])(=[O:8])=[O:7])=[CH:13][CH:12]=3)[N:15]=2)[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:27][CH:26]=2)[CH:22]=1

Komponenten

3

Edukt 1

HCID 247598725-{2-[6-Methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-thiazol-4-yl}-thiophene-2-sulfonic acid tert-butylamide

Produkt 1

HCID 574690445-{2-[6-Methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-thiazol-4-yl}-thiophene-2-sulfonic acid amideAusbeute 83,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

To 5-{2-[6-methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-thiazol-4-yl}-thiophene-2-sulfonic acid tert-butylamide (example 324) (0.100 g, 0.186 mmol) was added TFA (10 mL) and the reaction mixture was stirred at 23° C. for 16 h. The mixture was evaporated to dryness and partitioned between EtOAc and saturated NaHCO3 solution, the organic layer was dried over Na2SO4. Removal of the solvent in vacuum left a crude product which was triturated with diethyl ether to give the title compound as a white solid (0.075 g, 83%). MS (ISP) 482.3 [(M+H)+].

Aufarbeitung

  1. customThe mixture was evaporated to dryness
  2. custompartitioned between EtOAc and saturated NaHCO3 solution
  3. dry with materialthe organic layer was dried over Na2SO4
  4. customRemoval of the solvent in vacuum
  5. waitleft a crude product which
  6. customwas triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-d4c76ddf41444a99a207c4751579b670
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183262B2

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