Acetic Acid → HCID 69957824, Verbindung

HRID 1263540

Reaktionsgleichung

Reaktionsgleichung von HRID 1263540
[N+:1]([C:4]1[C:5]([NH2:11])=[C:6]([NH2:10])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[NH2:12][C:13]1[C:21]([NH2:22])=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([OH:17])=[O:16].[ClH:23].Cl.[C:25](=N)(OCC)[CH2:26][C:27](=N)OCC.C(O)(=O)C>Cl>[ClH:23].[ClH:23].[NH2:10][C:6]1[C:5]2[N:11]=[C:25]([CH2:26][C:27]3[NH:22][C:21]4[CH:20]=[CH:19][CH:18]=[C:14]([C:15]([OH:17])=[O:16])[C:13]=4[N:12]=3)[NH:1][C:4]=2[CH:9]=[CH:8][CH:7]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 73106Diethyl malonimidateHCID 1980692,3-Diaminobenzoic acidHCID 43595253-Nitro-1,2-phenylenediamine

Produkt 1

HCID 69957824HCID 69957824, VerbindungAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. customThe following components were reacted
  2. additionThe crude mixture of three compounds
  3. custompurified by preparative HPLC (2 to 40% acetonitrile (with 0.1% TFA) over 60 minutes)
  4. dry with materialdrying cycles with dilute HCl

Quellen und Nachweise

ORD-Eintrag
ord-db80e3c1fae54be495817b8bab8e2ca4
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06541486B1

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