Benzimidazole → 2-(1H-Benzimidazol-1-yl)-4-({[2-(trifluoromethyl)phenyl]methyl}-oxy)-1,3-thiazole-5-carboxamide

HRID 227661Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 227661
Cl[C:2]1[S:3][C:4]([C:19]([NH2:21])=[O:20])=[C:5]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([F:18])([F:17])[F:16])[N:6]=1.[N:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[NH:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[N:22]1([C:2]2[S:3][C:4]([C:19]([NH2:21])=[O:20])=[C:5]([O:7][CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:15]([F:18])([F:17])[F:16])[N:6]=2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[CH:23]1

Komponenten

6

Edukt 3

HCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 57756681HCID 57756681, Verbindung

Produkt 1

HCID 115389692-(1H-Benzimidazol-1-yl)-4-({[2-(trifluoromethyl)phenyl]methyl}-oxy)-1,3-thiazole-5-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 2-chloro-4-({[2-(trifluoromethyl)phenyl]methyl}oxy)-1,3-thiazole-5-carboxamide (0.050 g, 0.14 mmol) and benzimidazole (0.010 g, 0.08 mmol) in DMF (4 mL) was heated at 75° C. in the presence of K2CO3 (0.011 g, 0.08 mmol) for 12 h. After the reaction mixture had cooled to rt, it was diluted with EtOAc (10 mL), washed with H2O (4×10 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by preparative HPLC to afford the title compound. 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 7.96 (d, J=7.7 Hz, 1H), 7.88 (d, J=7.7 Hz, 1H), 7.77 (d, J=7.7 Hz, 1H), 7.67-7.59 (m, 2H), 7.54-7.40 (m, 3H), 6.80 (bs, 1H), 5.82 (s, 2H), 5.63 (bs, 1H). MS m/z 419 (m+1).

Aufarbeitung

  1. washwashed with H2O (4×10 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-cb67e2b62d5244fea89b1a191654e953
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560568B2

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