1,1'-Carbonyldiimidazole → 2-(3-[1,3]dioxolan-2-ylmethylphenyl)-1H-benzimidazole-4-carboxamide

HRID 736694Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 736694
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10](O)=O.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.Cl.[NH2:30][C:31]1[C:39]([NH2:40])=[CH:38][CH:37]=[CH:36][C:32]=1[C:33]([NH2:35])=[O:34]>N1C=CC=CC=1.CN(C)C=O>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][C:7]1[CH:8]=[C:9]([C:10]2[NH:40][C:39]3[CH:38]=[CH:37][CH:36]=[C:32]([C:33]([NH2:35])=[O:34])[C:31]=3[N:30]=2)[CH:13]=[CH:14][CH:15]=1

Komponenten

6

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 247269923-(1,3-Dioxolan-2-ylmethyl)benzoic acidHCID 534228072,3-Diaminobenzamide dihydrochloride

Produkt 1

HCID 685329682-(3-[1,3]dioxolan-2-ylmethylphenyl)-1H-benzimidazole-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3-(1,3-dioxolan-2-ylmethyl)benzoic acid (1.0 g, 4.80 mmol) in a mixture of pyridine (5 mL) and N,N-dimethylformamide (5 mL) was treated with 1,1′-carbonyldiimidazole (0.856 g, 5.28 mmol) at 45° C. for 2 hours. 2,3-diaminobenzamide dihydrochloride (synthesized as described in U.S. Pat. No. 6,737,421, column 11, EXAMPLE 2, step (e), 1.08 g, 4.80 mmol) was added and the mixture stirred at ambient temperature overnight. The mixture was concentrated and the residue purified by flash chromatography on silica gel with 10% methanol in 2:1 ethyl acetate/hexane. The product was dissolved in acetic acid (20 mL) and the solution heated at 60° C. for 2 hours and at 80° C. for 1.5 hours, cooled and concentrated and the residue partitioned between ethyl acetate and sodium bicarbonate solution. The organic phase was concentrated and the residue purified on silica gel with 10% methanol in 2:1 ethyl acetate/hexane to give 1.13 g of the title compound. MS (APCI) m/z 324 (M+H)+.

Aufarbeitung

  1. addition6,737,421, column 11, EXAMPLE 2, step (e), 1.08 g, 4.80 mmol) was added
  2. concentrationThe mixture was concentrated
  3. customthe residue purified by flash chromatography on silica gel with 10% methanol in 2:1 ethyl acetate/hexane
  4. dissolutionThe product was dissolved in acetic acid (20 mL)
  5. temperaturethe solution heated at 60° C. for 2 hours and at 80° C. for 1.5 hours
  6. temperaturecooled
  7. concentrationconcentrated
  8. customthe residue partitioned between ethyl acetate and sodium bicarbonate solution
  9. concentrationThe organic phase was concentrated
  10. customthe residue purified on silica gel with 10% methanol in 2:1 ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-4f666f28f3d7411483a7b720ca25ab08
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595406B2

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