Process for preparing substituted benzoyl cyanide amidinohydrazones

• US 20010025118A1
• Filed: 02/22/2001
• Published: 09/27/2001
• Est. Priority Date: 02/25/2000
• Status: Active Grant

• Current Assignee: Chemagis, Ltd (Wavelength Pharmaceuticals Ltd.)
• Original Assignee: Chemagis, Ltd (Wavelength Pharmaceuticals Ltd.)
• Inventors: Kaspi, Joseph, Lexmer, Jael, Nadaka, Vladimir
• Granted Patent: US 6,329,521 B2
• Time in Patent Office: Days
• US Class Current: 558/408
• CPC Class Codes: C07C 281/18 the other nitrogen atom being further doubly-bound to a carbon atom, e.g. guanylhydrazones
• CPC Class Codes: C07D 249/14 Nitrogen atoms

Abstract

The present invention provides a process for preparing a compound of the general formula (I):

wherein R₁ to R₅ are independently selected from hydrogen, halogen, C_1-6 alkyl, C_2-6 alkenyl, C_2-6 alkynyl or C_1-6 alkoxy, all optionally substituted by one or more of halogen, hydroxy and aryl groups, as well as being independently selected from amino, mono- or disubstituted amino, alkenyloxy, acyl, acyloxy, cyano, nitro, aryl and alkylthio groups, which process comprises reacting a compound of the general formula (II):

wherein R₁ to R₅ are as defined in formula (I), with aminoguanidine bicarbonate in a mixture of a water-soluble solvent and polyphosphoric acid.

Claims

1. A process for preparing a compound of the general formula (I):

wherein R₁ to R₅ are independently selected from hydrogen, halogen, C_1-6 alkyl, C_2-6 alkenyl, C_2-6 alkynyl or C_1-6 alkoxy, all optionally substituted by one or more of halogen, hydroxy and aryl groups, as well as being independently selected from amino, mono- or disubstituted amino, alkenyloxy, acyl, acyloxy, cyano, nitro, aryl and alkylthio groups, which process comprises reacting a compound of the general formula (II);

wherein R₁ to R₅ are as defined in formula (I), with aminoguanidine bicarbonate in a mixture of a water-soluble solvent and polyphosphoric acid.

2. A process according to

claim 1

wherein the amount of aminoguanidine bicarbonate is more than 1 equivalent per 1 equivalent of the compound of formula (II).

3. A process according to

claim 1

wherein the amount of polyphosphoric acid is from 4 to 8 g per one gram of the compound of formula (II).

4. A process according to

claim 1

wherein said water-soluble solvent is acetonitrile.

5. A process according to

claim 1

wherein the reaction of the compound of formula (II) with aminoguanidine bicarbonate is carried out at a temperature of about 25-150°

C.

6. A process according to

claim 1

wherein the compound of formula (I) is 2,3-Dichlorobenzoyl cyanide amidinohydrazone.