Adjudin synthesis

Yield:-

Reaction Conditions:

with hydrazine hydrate in acetic acid

Steps:

2 1-(2,4-dichlorobenzyl)-indazole-3-carbohydrazide (AF-2364) (I: X=Y=--Cl, R=--CONHNH2)
EXAMPLE 2 1-(2,4-dichlorobenzyl)-indazole-3-carbohydrazide (AF-2364) (I: X=Y=--Cl, R=--CONHNH₂) To a solution of 1-(2,4-dichlorobenzyl)-indazole-3-carboxylic acid methyl ester (12.5 g) in acetic acid (25 ml), at the temperature of 100° C. and under stirring, a solution of 85% hydrazine hydrate (100 ml) was slowly added. After 1 hour at reflux temperature the reaction mixture was cooled and filtered. The obtained solid was washed with H₂ O (2*150 ml) and recrystallized from ethyl alcohol to give the title compound (11.5 g), m.p.161-162° C. ¹ H NMR (DMSO, δ); 4.50 (s, 2H, NH₂); 1.96 (s, 2H, CH₂ -Ar); 6.8-8.3 (m, 7H, Ar); 9.6 (s, 1 H, NH).

References:

Angelini Pharmaceuticals Inc. US6001865, 1999, A

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