Some common heterocyclic compound, 626248-56-4, name is 3-(2H-1,2,3-Triazol-2-yl)aniline, molecular formula is C8H8N4, 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. Formula: C8H8N4
The mixture of tert-butyl (1S,2S)-2-(4-chloro-5-cyanopyrimidin-2-ylamino)-3,3-difluorocyclohexylcarbamate (A17) (51 mg, 0.13 mmol), 3-(2H-1,2,3-triazol-2-yl)aniline (43 mg, 0.26 mmol), fine powder Cs2C03 (130 mg, 0.40 mmol), Q-Phos (21 mg, 0.03 mmol) and Pd(dba)2 (18 mg, 0.03 mmol) in 15 mL toluene was degassed using argon stream and stirred at 105C under argon atmosphere for overnight. It was diluted with 100 mL EtOAc, filtered through celite, concentrated in vacuo and subjected to flash column to isolate tert-butyl (1S,2S)- 2-(4-(3 -(2H-1,2,3 -triazol-2-yl)phenylamino)-5 -cyanopyrimidin-2-ylamino)-3,3 – difluorocyclohexylcarbamate.lt was treated with 5 mL TFA and 1 mL concentrate H2SO4 at 80C for 45 m. It was cooled to RT. To it was added 5 mL water. The mixture was stirred, cooled, filtered and subjected to reverse phase preparative HPLC to isolate the title compound. MS found for C19H21F2N90 as (M+H)+ 430.4. UV: lambda=249 nm.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 626248-56-4, its application will become more common.
Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; JIA, Zhaozhong J.; KANE, Brian; XU, Qing; BAUER, Shawn M.; SONG, Yonghong; PANDEY, Anjali; DICK, Ryan; WO2013/78468; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics