1,1'-Carbonyldiimidazole → HCID 68536364, Verbindung

HRID 736704Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 736704
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:15]=[CH:14][C:10]([C:11](O)=O)=[C:9]([F:16])[CH:8]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.Cl.[NH2:31][C:32]1[C:40]([NH2:41])=[CH:39][CH:38]=[CH:37][C:33]=1[C:34]([NH2:36])=[O:35]>N1C=CC=CC=1.CN(C=O)C>[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:15]=[CH:14][C:10]([C:11]2[NH:41][C:40]3[CH:39]=[CH:38][CH:37]=[C:33]([C:34]([NH2:36])=[O:35])[C:32]=3[N:31]=2)=[C:9]([F:16])[CH:8]=1

Komponenten

6

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 534228072,3-Diaminobenzamide dihydrochlorideHCID 68533538HCID 68533538, Verbindung

Produkt 1

HCID 68536364HCID 68536364, VerbindungAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of EXAMPLE 22B (770 mg, 3.4 mmol) in pyridine (5 mL) and N,N′-dimethylformamide (10 mL) was treated with 1,1′-carbonyldiimidazole (763 mg, 3.4 mmol) at 40° C. for 30 minutes. 2,3-Diaminobenzamide dihydrochloride (826 mg, 5.1 mmol) was added and the mixture stirred at ambient temperature overnight. The mixture was concentrated and the residue refluxed overnight in 20 mL of xylene and 2 mL of acetic acid. After cooling and concentration, the residue was purified by flash chromatography on silica gel using ethyl acetate to give the title compound (550 mg, 50%). MS (DCI/NH3) m/z 342 (M+H)+.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. temperaturethe residue refluxed overnight in 20 mL of xylene
  3. temperatureAfter cooling
  4. concentrationconcentration
  5. customthe residue was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f63acb6057c5474a94aee2da4e8bbff2
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595406B2

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