1,1'-Carbonyldiimidazole → 5-Acetylthiophene-2-carboxylic acid (2-amino-3-carbamoylphenyl)amide

HRID 736692Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 736692
[C:1]([C:4]1[S:8][C:7]([C:9]([OH:11])=O)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.Cl.[NH2:26][C:27]1[C:35]([NH2:36])=[CH:34][CH:33]=[CH:32][C:28]=1[C:29]([NH2:31])=[O:30]>N1C=CC=CC=1.CN(C)C=O>[NH2:26][C:27]1[C:28]([C:29](=[O:30])[NH2:31])=[CH:32][CH:33]=[CH:34][C:35]=1[NH:36][C:9]([C:7]1[S:8][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][CH:6]=1)=[O:11]

Komponenten

6

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 37427275-Acetylthiophene-2-carboxylic acidHCID 534228072,3-Diaminobenzamide dihydrochloride

Produkt 1

HCID 673537955-Acetylthiophene-2-carboxylic acid (2-amino-3-carbamoylphenyl)amideAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To a solution of 5-acetylthiophene-2-carboxylic acid (1.80 g, 10.55 mmol) in pyridine (12 mL) and N,N-dimethylformamide (12 mL) was added 1,1′-carbonyldiimidazole (1.88 g, 11.60 mmol) and the mixture stirred at 45° C. for 4 hours. 2,3-Diaminobenzamide dihydrochloride (synthesized as described in U.S. Pat. No. 6,737,421, column 11, EXAMPLE 2, step (e), 2.36 g, 10.55 mmol) was added and the mixture was stirred at ambient temperature overnight. The reaction mixture was concentrated and the residue partitioned between ethyl acetate and water. The resulting yellow solid was collected by filtration, washed with water and ethyl acetate and dried to give the title compound (2.91 g, 91%). MS (APCI): 304 (M+1)+.

Aufarbeitung

  1. addition6,737,421, column 11, EXAMPLE 2, step (e), 2.36 g, 10.55 mmol) was added
  2. stirringthe mixture was stirred at ambient temperature overnight
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue partitioned between ethyl acetate and water
  5. filtrationThe resulting yellow solid was collected by filtration
  6. washwashed with water and ethyl acetate
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ac3744e0456f4fa2b15e8b887e355057
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595406B2

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