Reacción #58071

Ecuación de reacción

5-(2-amino-5-oxo-3,5-dihydro-imidazol-4-ylidene)-7-bromo-3,4,5,10-tetrahydro-2H-azepino[3,4-b]indol-1-one TFA salt

sodium acetate trihydrate

→

5-(2-amino-5-oxo-3.5-dihydro-imidazol-4-ylidene)-3,4,5,10-tetrahydro-2H-azepino[3,4-b]indol-1-one

Disolventes

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe catalyst is removed by filtration
2. 2
   ConcentraciónThe solution is concentrated
3. 3
   Otrothe residue is purified by HPLC (C18 column, eluted with CH3CN/H2O with 0.05% TFA)

Procedimiento

To a solution of 5-(2-amino-5-oxo-3,5-dihydro-imidazol-4-ylidene)-7-bromo-3,4,5,10-tetrahydro-2H-azepino[3,4-b]indol-1-one TFA salt (13 mg, 0.027 mmol), in MeOH (5 mL) is added sodium acetate trihydrate (24 mg, 0.18 mmol) and 10% Pd/C (4.5 mg). It is stirred at room temperature under a hydrogen atmosphere overnight and then the catalyst is removed by filtration. The solution is concentrated and the residue is purified by HPLC (C18 column, eluted with CH3CN/H2O with 0.05% TFA) to give 5-(2-amino-5-oxo-3.5-dihydro-imidazol-4-ylidene)-3,4,5,10-tetrahydro-2H-azepino[3,4-b]indol-1-one; 1H NMR (DMSO-d6) δ 3.30-3.36 (m, 4H), 7.20 (t, 1H, J=7.6 Hz), 7.33 (t, 1H, J=7.2 Hz), 7.53 (t, 1H, J=7.6 Hz), 7.58 (d, 1H, J=7.2 Hz), 8.36 (t, 1H, J=2.4 Hz), 9.20 (bs, 1H), 10.37 (bs, 1H), 12.45 (s, 1H); m/z [M++1] 296.1.

Fuente