Some common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, molecular formula is C6H3Cl2N3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Product Details of 918538-05-3
69A. Preparation of 2-chloro-N-(3-cyclopropyl-1H-pyrazol-5-yl)pyrrolo[1,2-f][1,2,4]triazin-4-amine A solution of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (1.5 g, 5.3 mmol) in i-PrOH (15 mL) was treated with 3-cyclopropyl-1H-pyrazol-5-amine (657 mg, 5.3 mmol) and DIEA (0.92 mL, 5.3 mmol). The reaction was stirred overnight at ambient temperature and then filtered. The filter cake was washed with cold i-PrOH and dried under vacuum to afford 69A as a solid (1.3 g, 90%). HPLC tR=3.301 min (YMC S5 Combiscreen ODS 4.6*50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min gradient, monitored at 254 nm). [M+H]+=275.37. A solution of 2-chloro-N-(3-cyclopropyl-1H-pyrazol-5-yl)pyrrolo[1,2-f][1,2,4]triazin-4-amine (1A) (100 mg, 0.36 mmol) and piperidine-4-carboxamide (467 mg, 3.6 mmol) in NMP (1 mL) was heated in a microwave safe tube (CEM Corporation, 10 mL) at 100 C. for 40 minutes using 300 W continuous power. The reaction was diluted with EtOAc (10 mL) and washed with 10% aqueous LiCl solution (2*10 mL). The organic layers were combined and dried (Na2SO4), filtered and concentrated. The crude product was purified by preparative reversed-phase HPLC to afford the title compound (23 mg, 15%). HPLC tR=2.398 min (YMC S5 Combiscreen ODS 4.6*50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min gradient, monitored at 254 nm).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 918538-05-3, its application will become more common.
Reference:
Patent; Bristol-Myers Squibb Company; US2008/45496; (2008); A1;,
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