Trifluoroacetic acid → HCID 178510241, Verbindung

HRID 1875163Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1875163
[Cl:1][C:2]1[N:3]=[CH:4][N:5](COCC[Si](C)(C)C)[C:6]=1[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([C:29]#[N:30])[CH:20]=2)[C:12]=1[F:31])=[O:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][C:19]2[CH:24]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:22]=[C:21]([C:29]#[N:30])[CH:20]=2)[C:12]=1[F:31])=[O:8]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 866449424-chloro-N-[(4-chloro-3-{[3-cyano-5-(trifluoromethyl)phenyl]oxy}-2-fluorophenyl)methyl]-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide

Produkt 1

HCID 178510241HCID 178510241, VerbindungAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-chloro-N-[(4-chloro-3-{[3-cyano-5-(trifluoromethyl)phenyl]oxy}-2-fluorophenyl)methyl]-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (97 mg, 0.161 mmol) in DCM (7 ml) was added TFA (3 ml) and the reaction mixture was stirred at rt for 2 hours. The reaction mixture was quenched with saturated sodium bicarbonate and the organic layer was separated. The solvent was removed and the crude material was purified via silica gel chromatography to give 4-chloro-N-[(4-chloro-3-{[3-cyano-5-(trifluoromethyl)phenyl]oxy}-2-fluorophenyl)methyl]-1H-imidazole-5-carboxamide (45 mg, 0.095 mmol, 59% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.82 (s, 1H), 7.69 (s, 1H), 7.47-7.53 (m, 2H), 7.35-7.42 (m, 2H), 4.63 (s, 2H). LC-MS (ES+) m/z 473.07, [M+H].

Aufarbeitung

  1. customThe reaction mixture was quenched with saturated sodium bicarbonate
  2. customthe organic layer was separated
  3. customThe solvent was removed
  4. customthe crude material was purified via silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3bdcb7e4e392469ab161182349e31e2d
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

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