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Trifluoroacetic acid → 3'-[4-(5-Chloro-thiophen-2-yl)-6-trifluoromethyl-pyrimidin-2-yl]-biphenyl-3-sulfonic acid amide

HRID 906267
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 906267
C([NH:5][S:6]([C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[N:26]=[C:25]([C:27]4[S:28][C:29]([Cl:32])=[CH:30][CH:31]=4)[CH:24]=[C:23]([C:33]([F:36])([F:35])[F:34])[N:22]=3)[CH:16]=2)[CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[Cl:32][C:29]1[S:28][C:27]([C:25]2[CH:24]=[C:23]([C:33]([F:34])([F:35])[F:36])[N:22]=[C:21]([C:17]3[CH:16]=[C:15]([C:11]4[CH:12]=[CH:13][CH:14]=[C:9]([S:6]([NH2:5])(=[O:8])=[O:7])[CH:10]=4)[CH:20]=[CH:19][CH:18]=3)[N:26]=2)=[CH:31][CH:30]=1
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Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 673930193'-[4-(5-Chloro-thiophen-2-yl)-6-trifluoromethyl-pyrimidin-2-yl]-biphenyl-3-sulfonic acid tert-butylamide

Produkt 1

HCID 250971933'-[4-(5-Chloro-thiophen-2-yl)-6-trifluoromethyl-pyrimidin-2-yl]-biphenyl-3-sulfonic acid amideAusbeute 65,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a cooled and stirred solution of 3′-[4-(5-chloro-thiophen-2-yl)-6-trifluoromethyl-pyrimidin-2-yl]-biphenyl-3-sulfonic acid tert-butylamide (0.22 g) in dichloromethane (5 ml) was added TFA (5 ml) and the reaction mixture was allowed to stir at room temperature for 15 h. The mixture was evaporated, poured into saturated NaHCO3 solution (20 ml) and extracted with ethyl acetate (2×30 ml). The combined organic layers were washed with brine (20 ml), dried (MgSO4) and evaporated. Further purification by flash chromatography on silica gel (ethyl acetate/heptane) and crystallization (MeOH) yielded the title compound as a light yellow solid (0.13 g, 27%). MS (ISN) 494.3 [(M−H)−]; mp 226.5° C.

Aufarbeitung

  1. temperatureTo a cooled
  2. customThe mixture was evaporated
  3. additionpoured into saturated NaHCO3 solution (20 ml)
  4. extractionextracted with ethyl acetate (2×30 ml)
  5. washThe combined organic layers were washed with brine (20 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customFurther purification by flash chromatography
  9. customon silica gel (ethyl acetate/heptane) and crystallization (MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-f862b8cf90f6460093c4443cd8743f38
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08012986B2

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