Reacción #1340625

Ecuación de reacción

MeONa

enamine

methyl [(4Z)-1-benzyl-4-{2-(3-methoxyphenyl)-1-[(pyridin-2-ylmethyl)amino]ethylidene}-5-oxo-4,5-dihydro-1H-pyrazol-3-yl]acetate

→

2-benzyl-4-(3-methoxybenzyl)-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione

Rendimiento 43.0%

Disolventes

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe reaction mixture was concentrated in vacuum
2. 2
   workup.DISSOLUTIONthe crude was dissolved in ethyl acetate (80 ml)
3. 3
   Extracciónextracted with water (30 ml*3)
4. 4
   Extracciónextracted with ethyl acetate (30 ml*3)
5. 5
   Secadothe combined organic layer was dried over Na2SO4
6. 6
   Otropurified by TLC

Procedimiento

The above obtained methyl [(4Z)-1-benzyl-4-{2-(3-methoxyphenyl)-1-[(pyridin-2-ylmethyl)amino]ethylidene}-5-oxo-4,5-dihydro-1H-pyrazol-3-yl]acetate (Compound of Formula (VIII) was treated with freshly prepared MeONa in MeOH (2M, 20 ml). The solution was stirred at room temperature until disappearance of the starting enamine (t=0.5-2 h). The reaction mixture was concentrated in vacuum to eliminate MeOH and the crude was dissolved in ethyl acetate (80 ml), extracted with water (30 ml*3). Then the combined inorganic layer was acidified to pH=6, extracted with ethyl acetate (30 ml*3), the combined organic layer was dried over Na2SO4, purified by TLC yielding the final product 2-benzyl-4-(3-methoxybenzyl)-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione as yellow oil (65 mg, yield: 43%). 1HNMR (400 MHz, DMSO-d6): 3.635 (s, 3H); 4.702 (s, 2H); 4.860 (s, 2H); 5.274 (s, 2H), 5.696 (s, 1H); 6.646-6.716 (m, 3H), 7.104-7.144 (m, 2H); 7.277-7.416 (m, 6H); 7.823-7.859 (t, 1H); 8.492-8.501 (d, 1H). MS (ESI+): 453.2; MS (ESI): 451.2.

Fuente