Reaktion #1350722

Reaktionsgleichung

acetic acid

3-nitro-1,2-phenylenediamine

2,3-diaminobenzoic acid

diethyl malonimidate dihydrochloride

→

2-[(4-amino-1H-benzimidazol-2-yl)methyl]-1H-benzimidazole-4-carboxylic acid dihydrochloride

Ausbeute 15.0%

Lösungsmittel

HCl

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe following components were reacted
2. 2
   workup.ADDITIONThe crude mixture of three compounds
3. 3
   Sonstigepurified by preparative HPLC (2 to 40% acetonitrile (with 0.1% TFA) over 60 minutes)
4. 4
   Trocknendrying cycles with dilute HCl

Vorschrift

The following components were reacted according to General Procedure 1, above: 3-nitro-1,2-phenylenediamine (0.50 g; 3.26 mmoles) 2,3-diaminobenzoic acid (0.40 g; 3.26 mmoles), diethyl malonimidate dihydrochloride (1.1 eq.; 0.83 g; 3.60 mmoles) and acetic acid (25 mL). The crude mixture of three compounds was then reduced according to General Procedure 2, above. The crude solid was taken up in 10 mL of dilute HCl, purified by preparative HPLC (2 to 40% acetonitrile (with 0.1% TFA) over 60 minutes) and converted to the HCl salt by three freeze drying cycles with dilute HCl. This procedure gave 0.103 g of pure 2-[(4-amino-1H-benzimidazol-2-yl)methyl]-1H-benzimidazole-4-carboxylic acid dihydrochloride in 8% yield. It had MS: m/z=308.2 [M+1] amu and gave one peak on HPLC at both 210 and 280 nm (10.20 minutes using the JWTFACN gradient).

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