1063734-49-5Relevant articles and documents
Kilogram-Scale Preparation of an Aminopyrazole Building Block via Copper-Catalyzed Aryl Amidation
Baldwin, Aaron F.,Caporello, Michaella A.,Chen, Guoyong,Goetz, Adam E.,Hu, Weifeng,Jin, Chengfeng,Knopf, Kevin M.,Li, Zhifeng,Lu, Cuong V.,Monfette, Sebastien,Puchlopek-Dermenci, Angela L. A.,Shi, Feng
, p. 1065 - 1073 (2021)
We describe a scalable method for preparing an aminopyrazole building block using copper-catalyzed amidation with acetamide as an ammonia surrogate. This procedure provides an alternative to the standard nitration/reduction sequence and avoids energetic intermediates, specialized hydrogenation equipment, and potentially genotoxic impurities that arise from nitro reduction. The chemistry has been successfully scaled to produce >50 kg of the target compound and demonstrate the viability of this alternative route.
U.V. and 15N N.M.R. Integrated Study of the Protonation of Aminoazoles
Garrone, Adele,Fruttero, Roberta,Tironi, Carla,Gasco, Alberto
, p. 1941 - 1946 (2007/10/02)
The behaviour on protonation of a series of 3-, 4-, and 5-aminoisoxazoles has been studied by 15N n.m.r. spectroscopy.The results confirm that the first protonation site in the 3- and 5-amino derivatives is located at the endocyclic nitrogen atom, while in 4-amino derivatives it is at the exocyclic nitrogen.In addition, the protonation of 3-, 4-, and 5-amino substituted 1-methyl- and 1-phenyl-pyrazoles has been investigated by an integrated u.v. and 15N n.m.r. approach.The first protonation site in the 5-amino derivatives is the pyridine-like endocyclic nitrogen, while in the 4-amino derivatives it is the exocyclic nitrogen.The 3-amino series behaves exceptionally because a tautomeric equilibrium is possible between the endocyclic and exocyclic monocations.In sulphuric acid the position of this equilibrium is dependent on H2SO4 concentration.Diprotonation of these derivatives in concentrated sulphuric acid solutions has also been studied.