تفاعل #44011

معادلة التفاعل

phenylenediamine

CH2Cl2

Thionyl chloride

Compound 79

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

→

80

المردود 13.0%

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

المردود 13.0%

المذيبات

EtOH

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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)+.

المصدر