Reacción #44011

Ecuación de reacción

phenylenediamine

CH2Cl2

Thionyl chloride

Compound 79

5-(4-chlorophenylsulfonyl)-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-4-carbaldehyde

→

80

Rendimiento 13.0%

4-(1H-benzo[d]imidazol-2-yl)-5-(4-chlorophenylsulfonyl)-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine

Rendimiento 13.0%

Disolventes

EtOH

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter the addition
2. 2
   workup.STIRRINGThe reaction stirred at room temperature for 18 hours
3. 3
   Filtraciónthe resulting suspension was filtered
4. 4
   ConcentraciónThe filtrate was concentrated in vacuo
5. 5
   Otrothe resulting residue was purified by preparative HPLC

Procedimiento

A flask was charged with silica (0.06 g) and CH2Cl2 (5 mL). Thionyl chloride (0.015 mL) was added dropwise. After the addition was complete, the reaction stirred at room temperature for 1 hour. Compound 79 (0.05 g, 0.15 mmol) was added, followed by phenylenediamine (0.017 g, 0.15 mmol). The reaction stirred at room temperature for 18 hours. The mixture was diluted with EtOH and the resulting suspension was filtered. The filtrate was concentrated in vacuo and the resulting residue was purified by preparative HPLC using Method [1] to yield 7.8 mg (13%) 80 as a white powder. 1H NMR (CD3OD) δ 9.13 (s, 1H), 8.33 (s, 1H), 8.05-8.01 (m, 2H), 7.85-7.73 (m, 2H), 7.66 (d, J=8.7 Hz, 2H), 7.39 (d, J=9.0 Hz), 3.42-3.34 (m, 3H); MS (m/z) 414.0 (M+H)+.

Fuente