1,1'-Carbonyldiimidazole → 2-(4-[1,3] Dioxolan-2-yl-2-fluorophenyl)-1h-benzimidazole-4-carboxamide

HRID 1673149Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1673149
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:14]=[CH:13][C:9]([C:10](O)=O)=[C:8]([F:15])[CH:7]=1.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[C:6]1[CH:14]=[CH:13][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)=[C:8]([F:15])[CH:7]=1

Komponenten

6

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 534228072,3-Diaminobenzamide dihydrochlorideHCID 673539164-(1,3-Dioxolan-2-yl)-2-fluorobenzoic acid

Produkt 1

HCID 673529522-(4-[1,3] Dioxolan-2-yl-2-fluorophenyl)-1h-benzimidazole-4-carboxamideAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of EXAMPLE 17D (1.5 g, 7.1 mmol) in pyridine (5 mL) and N,N-dimethylformamide (20 mL) was treated with 1,1′-carbonyldiimidazole (1.4 g, 8.5 mmol) at 40° C. for 30 minutes. 2,3-Diaminobenzamide dihydrochloride (synthesized as described in U.S. Pat. No. 6,737,421, column 11, EXAMPLE 2, step (e), 1.58 g, 7.1 mmol) was added and the mixture stirred at ambient temperature overnight. Solvents were removed and the residue was stirred in acetic acid (10 mL) at 80° C. overnight. After concentration, the residue was purified by flash chromatography on silica gel (ethyl acetate) to give 500 mg (22%) of the title compound. MS (DCI/NH3) m/z 329 (M+H)+.

Aufarbeitung

  1. addition6,737,421, column 11, EXAMPLE 2, step (e), 1.58 g, 7.1 mmol) was added
  2. customSolvents were removed
  3. stirringthe residue was stirred in acetic acid (10 mL) at 80° C. overnight
  4. concentrationAfter concentration
  5. customthe residue was purified by flash chromatography on silica gel (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-691370e5d1e24499b70660eb9baba27e
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07999117B2

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