반응 #510160
ord-369d0a3e05424cedb61b679c473739c8
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후처리
- 1기타The crude product was purified by ion exchange chromatography
- 2세척The desired product was eluted from the column
- 3기타were evaporated to dryness
- 4workup.ADDITIONTFA (5 mL) was added
- 5workup.STIRRINGThe reaction mixture was stirred for 1 hour
- 6기타the crude product was purified by ion exchange chromatography
- 7세척The desired product was eluted from the column
- 8기타were evaporated to dryness
- 9기타to afford the crude material as a white solid
- 10기타This material was triturated under cold methanol
실험 절차
O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.228 g) was added to 4-(tert-butoxycarbonylamino)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid (Intermediate 1) (0.181 g), (4-chlorophenyl)(cyclopropyl)methanamine (Intermediate 3) (0.091 g) and DIPEA (0.261 mL) in DMA (5 mL) at 25° C. The resulting solution was stirred at 50° C. for 1 hour. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7N ammonia/MeOH and pure fractions were evaporated to dryness. This crude material was suspended in dichloromethane (25 mL), and TFA (5 mL) was added. The reaction mixture was stirred for 1 hour, then the crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7N ammonia/MeOH and pure fractions were evaporated to dryness to afford the crude material as a white solid. This material was triturated under cold methanol to give the pure product, 4-amino-N-((4-chlorophenyl)(cyclopropyl)methyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide as a white solid (0.167 g, 79%).