Electric Literature of 70500-80-0,Some common heterocyclic compound, 70500-80-0, name is Ethyl 5-amino-1-methyl-1H-pyrazole-3-carboxylate, molecular formula is C7H11N3O2, 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.
A mixture of 6-chloro-N-cyclopropyl-8-((4-methoxybenzyl)(methyl) amino)imidazo [1 ,2-bjpyridazine-3 -carboxamide (id) (125 mg, 0.324 mmol), ethyl 5-amino-i-methyl- 1H-pyrazole-3 -carboxylate [Free based (sodium bicarbonate solutionlEtOAc) from HC1 salt purchased from Acorn Pharma. Tech.j (88 mg, 0.5 18 mmol), Pd2(dba)3 (29.7 mg, 0.032 mmol), XANTPHOS (37.5 mg, 0.065 mmol) and Cs2CO3 (422 mg, 1.296 mmol) in DMA (2 mL) was degassed by bubbling N2 through the mixture for 5 minutes. The reaction vessel was sealed and heated to 125 C for 2 hr. After cooling to rt, the reaxtion mixture was partitioned between EtOAc (50 ml) and water (50 ml). The organic layer was washed with 10%LiC1 solution (2 x 50 ml) and brine (50 ml). After drying (Na2SO4) and filtration the organic layer was concentrated toafford a tan solid that was chromatographed on a 12 gm ISCO silica gel cartridge, eluting with a 0-1 OO%EtOAc/Hex gradient. The pure fractions were concentrated to afford ethyl 5 -((3-(cyclopropylcarbamoyl)-8-((4-methoxybenzyl)(methyl)amino)imidazo [1,2- bjpyridazin-6-yl)amino)- 1-methyl-i H-pyrazole-3 -carboxylate (39a) (126 mg, 0.243 mmol, 75 % yield) as atan solid. LC retention time 2.77 mm [Cj. MS (E+) m/z: 519(MHj.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 5-amino-1-methyl-1H-pyrazole-3-carboxylate, its application will become more common.