Acetic Acid → HCID 18616881, Verbindung

HRID 1263537

Reaktionsgleichung

Reaktionsgleichung von HRID 1263537
[N+:1]([C:4]1[C:5]([NH2:11])=[C:6]([NH2:10])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[F:12][C:13]1[C:14]([NH2:20])=[C:15]([NH2:19])[CH:16]=[CH:17][CH:18]=1.[ClH:21].Cl.[C:23](=N)(OCC)[CH2:24][C:25](=N)OCC.C(O)(=O)C>Cl>[ClH:21].[ClH:21].[F:12][C:13]1[C:14]2[N:20]=[C:23]([CH2:24][C:25]3[NH:1][C:4]4[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=4[N:11]=3)[NH:19][C:15]=2[CH:16]=[CH:17][CH:18]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 73106Diethyl malonimidateHCID 27828353-Fluorobenzene-1,2-diamineHCID 43595253-Nitro-1,2-phenylenediamine

Produkt 1

HCID 18616881HCID 18616881, VerbindungAusbeute 32,6 %

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), 3-fluoro-1,2-phenylenediamine (0.41 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 product was taken up in 10 mL of dilute HCl, purified by preparative HPLC (25 to 75% acetonitrile (with 0.1% TFA) over 50 minutes) and converted to the HCl salt by three freeze drying cycles with dilute HCl. This procedure gave 0.208 g of pure 2-[(4-fluoro-1H-benzimidazol-2-yl)methyl]-1H-benzimidazol-4-ylamine dihydrochloride in 18% yield. It had MS: m/z=282.2 [M+1] amu and gave one peak on HPLC at both 210 and 280 nm (12.99 minutes using the JWTFACN gradient).

Aufarbeitung

  1. customThe following components were reacted
  2. additionThe crude mixture of three compounds
  3. custompurified by preparative HPLC (25 to 75% acetonitrile (with 0.1% TFA) over 50 minutes)
  4. dry with materialdrying cycles with dilute HCl

Quellen und Nachweise

ORD-Eintrag
ord-f967c17d980443448905e7c47cc9591f
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06541486B1

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