Trifluoroacetic acid → 5-{1-[4-(3-Methyl-4-trifluoromethyl-phenyl)-6-trifluoromethyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-thiophene-2-sulfonic Acid Amide

HRID 1928229Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1928229
C([NH:5][S:6]([C:9]1[S:10][C:11]([C:14]2[N:15]=[CH:16][N:17]([C:19]3[N:24]=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[C:27]([CH3:35])[CH:26]=4)[CH:22]=[C:21]([C:36]([F:39])([F:38])[F:37])[N:20]=3)[CH:18]=2)=[CH:12][CH:13]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH3:35][C:27]1[CH:26]=[C:25]([C:23]2[CH:22]=[C:21]([C:36]([F:37])([F:38])[F:39])[N:20]=[C:19]([N:17]3[CH:18]=[C:14]([C:11]4[S:10][C:9]([S:6]([NH2:5])(=[O:8])=[O:7])=[CH:13][CH:12]=4)[N:15]=[CH:16]3)[N:24]=2)[CH:30]=[CH:29][C:28]=1[C:31]([F:34])([F:33])[F:32]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 602094475-{1-[4-(3-methyl-4-trifluoromethyl-phenyl)-6-trifluoromethyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-thiophene-2-sulfonic acid tert-butyl amide

Produkt 1

HCID 574689755-{1-[4-(3-Methyl-4-trifluoromethyl-phenyl)-6-trifluoromethyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-thiophene-2-sulfonic Acid AmideAusbeute 64,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a cooled and stirred solution of 5-{1-[4-(3-methyl-4-trifluoromethyl-phenyl)-6-trifluoromethyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-thiophene-2-sulfonic acid tert-butyl amide (0.24 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 to dryness and purified by column chromatography on silica gel (dichloromethane/MeOH/NH4OH 80:10:1) and crystallization (MeOH/diethyl ether) to yield the title compound as a light yellow solid (0.14 g, 52%). MS (ISN) 532.3 [(M−H)−]; mp 260° C.

Aufarbeitung

  1. temperatureTo a cooled
  2. customThe mixture was evaporated to dryness
  3. custompurified by column chromatography on silica gel (dichloromethane/MeOH/NH4OH 80:10:1) and crystallization (MeOH/diethyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-0ec070504b444d40a680133a4dc04a98
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183262B2

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