Application of 152120-54-2,Some common heterocyclic compound, 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, molecular formula is C14H22N4O4, 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.
To a stirred solution of N,N?-di-Boc-pyrazologuanidine (1,0 g, 3,22 mmol) in dry THF (20 mL) under N2 atmosphere, PPh3 (1,27 g, 4,19 mmol) and crotyl alcohol (0,36 mL, 4,19 mmol) were added. The mixture was cooled to 0 Cand DIAD (0,91 mL, 4,84 mmol) was added dropwise. The mixture was stirred at 0 C for 15 min then at room temperature for 2 h, then it was diluted with AcOEt and washed with water. The aqueous phase was back-extracted with AcOEt. The combined organic phases were washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified with flash chromatography on silica gel, eluting with 10% AcOEt/Hex to give pure compound 9 (0.95 g, 95% yield). 1H NMR (400 MHz CDCl3) delta 7.89 (s, 1H), 7.66 (s, 1H), 6.37 (s, 1H), 5.60 (m, 2H), 4.18 (m, 2H), 1.62 (s, 3H), 1.44 (s, 9H), 1.22 (s, 9H). LC-MS(ES) m/z = 387.1 [M+Na]+, 365.1 [M+H]+.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, its application will become more common.
Reference:
Article; Borgini, Matteo; Orofino, Francesco; Truglio, Giuseppina I.; Balestri, Lorenzo; Botta, Maurizio; Arkivoc; vol. 2019; 4; (2019);,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics