2,4,6-Trichlorobenzaldehyde → 2-(2,4,6-Trichlorophenyl)-3H-benzoimidazole-5-carboxylic acid quinolin-2-ylamide

HRID 1514915Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1514915
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=O.[NH2:12][C:13]1[CH:14]=[C:15]([CH:29]=[CH:30][C:31]=1[NH2:32])[C:16]([NH:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1)=[O:17]>CS(C)=O>[N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[CH:28][C:19]=1[NH:18][C:16]([C:15]1[CH:29]=[CH:30][C:31]2[N:32]=[C:4]([C:3]3[C:2]([Cl:1])=[CH:9][C:8]([Cl:10])=[CH:7][C:6]=3[Cl:11])[NH:12][C:13]=2[CH:14]=1)=[O:17]

Komponenten

4

Edukt 2

HCID 53144572,4,6-TrichlorobenzaldehydeHCID 669657403,4-diamino-N-quinolin-2-yl-benzamide

Produkt 1

HCID 669656192-(2,4,6-Trichlorophenyl)-3H-benzoimidazole-5-carboxylic acid quinolin-2-ylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a stirred solution of 2,4,6-trichlorobenzaldehyde (150 mg, 0.72 mmol) and 3,4-diamino-N-quinolin-2-yl-benzamide (200 mg, 0.72 mmol) in DMSO (10 mL) was added FeCl3 (23 mg, 0.14 mmol). The solution was stirred at ambient temperature for 2 days. The reaction was quenched with water and the aqueous layer was extracted with EtOAc. The organic layer was washed with water, brine, dried with MgSO4, and filtered. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using heptane/EtOAc (1/3) as eluent to give the title compound as a white solid. 1H NMR (Methanol-d4, 400 MHz): δ 8.45 (m, 3H), 8.08 (d, 1H), 7.93 (m, 2H), 7.85 (s, 1H), 7.76 (s, 2H), 7.75 (m, 1H), 7.55 (m, 1H). MS (m/z) 467.0 (M+1); Retention time: 1.48 min (Method 10).

Aufarbeitung

  1. customThe reaction was quenched with water
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-de7ae132a5df4fdba741aa9bfbf1517a
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222248B2

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