反应 #165790

反应方程式

4-(5-amino-6-(hydrazinecarbonyl)pyrazin-2-yl)-N,N-dimethylbenzamide

2-chloroaniline

1,1′-thiocarbonyldiimidazole

1,1′-thiocarbonyldiimidazole

→

4-[5-amino-6-[[(2 chlorophenyl)carbamothioylamino]carbamoyl]pyrazin-2-yl]-N,N-dimethyl-benzamide

溶剂

dichloromethane

dichloromethane

water

dichloromethane

反应条件

后处理

1. 1
   workup.STIRRINGthe reaction mixture stirred at room temperature overnight
2. 2
   萃取extracted with dichloromethane (3×5 mL)
3. 3
   干燥The organic extracts were dried over MgSO4
4. 4
   过滤filtered
5. 5
   其他evaporated to dryness
6. 6
   其他to leave a yellow solid
7. 7
   workup.STIRRINGthe reaction mixture stirred at room temperature for 48 h
8. 8
   其他The reaction mixture was evaporated
9. 9
   其他triturated with EtOAc/Petrol/Ether

实验过程

A solution of 2-chloroaniline (31.85 mg, 41.15 μL, 0.2497 mmol) in dichloromethane (2 mL) was slowly added dropwise to a solution of 1,1′-thiocarbonyldiimidazole (53.39 mg, 0.2996 mmol) in dichloromethane (1.5 mL) and the resulting solution stirred at room temperature for 1 h. Additional 1,1′-thiocarbonyldiimidazole (8.9 mg, 0.05 mmol) was added, and the reaction mixture stirred at room temperature overnight. The reaction mixture diluted with water and extracted with dichloromethane (3×5 mL). The organic extracts were dried over MgSO4, filtered and evaporated to dryness to leave a yellow solid. The solid was re-dissolved in dichloromethane (1.5 mL) and 4-(5-amino-6-(hydrazinecarbonyl)pyrazin-2-yl)-N,N-dimethylbenzamide (75 mg, 0.2497 mmol) added and the reaction mixture stirred at room temperature for 48 h. The reaction mixture was evaporated to drymess and then triturated with EtOAc/Petrol/Ether to give a yellow solid, 4-[5-amino-6-[[(2 chlorophenyl)carbamothioylamino]carbamoyl]pyrazin-2-yl]-N,N-dimethyl-benzamide. This was re-dissolved in dichloromethane (1.5 mL) and EDC (71.81 mg, 0.3746 mmol) added and the resulting solution heated at 40° C. for 3 h. The reaction mixture was cooled to room temperature and concentrated in vacuo and the solid triturated with EtOAc and petroleum ether to yield the product as a yellow solid (28.9 mg, 26% yield); 1H NMR (400.0 MHz, DMSO) d 2.96 (s, 3H), 3.01 (s, 3H), 7.15-7.25 (m, 1H), 7.40-7.49 (m, 1H), 7.53 (d, 3H), 7.70 (br s, 2H), 8.11 (d, 3H), 8.89 (s, 1H) and 10.45 (s, 1H) ppm; MS (ES+) 436.11

来源