Hydrochloric Acid → 4-(1h-Imidazol-2-ylcarbamoyl)-1h-benzoimidazole-2-carboxylic acid

HRID 1910136Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1910136
[NH2:1][C:2]1[C:15]([NH2:16])=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([NH:6][C:7]1[NH:8][CH:9]=[CH:10][N:11]=1)=[O:5].Cl[C:18](Cl)(Cl)[C:19](N)=[O:20].Cl.[Li+].[OH-:26]>C(O)(=O)C.CO.C1COCC1>[NH:11]1[CH:10]=[CH:9][N:8]=[C:7]1[NH:6][C:4]([C:3]1[C:2]2[N:1]=[C:18]([C:19]([OH:20])=[O:26])[NH:16][C:15]=2[CH:14]=[CH:13][CH:12]=1)=[O:5]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 61144TrichloroacetamideHCID 669405262,3-Diamino-n-(1h-imidazol-2-yl)-benzamide

Produkt 1

HCID 669403914-(1h-Imidazol-2-ylcarbamoyl)-1h-benzoimidazole-2-carboxylic acidAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirring solution of 200 mg (0.92 mmol) of 2,3-diamino-N-(1H-imidazol-2-yl)-benzamide (synthesized as described in Intermediate-B) in 2.0 mL of acetic acid was added 200 mg (1.15 mmol) of 2,2,2-trichloroacetamide and stirring continued for 30 min at r.t. Then 0.5 mL of 1% HCl in methanol was added and stirred for another 45 min at r.t. Evaporation of the solvent gave the crude ester, which was dissolved in 4:1 THF and methanol (5 mL) and then 1.0 mL of 2N LiOH was added at r.t. The reaction mixture was stirred at r.t. for 30 min, the pH was adjusted to 3.0 and then extracted with ethyl acetate twice (2×25 mL). The combined organic solvents were dried, evaporated to provide 100 mg (40%) of 4-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazole-2-carboxylic acid, which was used, for the next step without further purification. LCMS: 272 (M+1)+.

Aufarbeitung

  1. stirringstirred for another 45 min at r.t
  2. customEvaporation of the solvent
  3. customgave the crude ester, which
  4. stirringThe reaction mixture was stirred at r.t. for 30 min
  5. extractionextracted with ethyl acetate twice (2×25 mL)
  6. customThe combined organic solvents were dried
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-a0ca6bcd64f5498f8ff05e43a78307ff
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598353B2

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