반응 #333432
ord-186476861138432f9c6b5794e599829b
반응 방정식
반응물
시약
용매
반응 조건
후처리
- 1기타to give a yellow solution
- 2workup.STIRRINGthe reaction was stirred at 0° C. for 30 min
- 3온도to warm to room temperature
- 4workup.STIRRINGstirred for 2 h
- 5기타The reaction mixture was quenched with 5 mL of brine and 10 mL of water
- 6추출extracted with ethyl acetate (2×30 mL)
- 7세척The combined organic layers were washed with water and brine
- 8기타dried
- 9농축concentrated in vacuo
- 10기타The crude material was purified by silica gel chromatography (0-10% methanol in dichloromethane)
실험 절차
2-(6-Chloro-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-2-methoxy-1-methyl-ethyl)-amide (80 mg, 0.16 mmol) was combined with DMF (8 mL) at 0° C. to give a yellow solution. Sodium hydride (60% in mineral oil, 19 mg, 0.47 mmol) was added and the reaction was stirred at 0° C. for 10 min. Dimethylaminoethyl bromide hydrobromide (54 mg, 0.23 mmol) was added and the reaction was stirred at 0° C. for 30 min, then allowed to warm to room temperature and stirred for 2 h. The reaction mixture was quenched with 5 mL of brine and 10 mL of water, then extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with water and brine, then dried and concentrated in vacuo. The crude material was purified by silica gel chromatography (0-10% methanol in dichloromethane) to afford 50 mg (55%) of 2-[6-chloro-1-(2-dimethylamino-ethyl)-1H-indazol-3-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-2-methoxy-1-methyl-ethyl)-amide as a foaming solid. MS: (M+H)+=587.