Electric Literature of 15963-46-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 15963-46-9, name is Methyl 3-chlorocyclobutanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
To a solution of 4-(1-(pentan-3-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrazine (0.100 g, 0.311 mmol) and methyl 3-chlorocyclobutanecarboxylate (0.0925 g, 0.622 mmol) in DMF (1.56 mE, 0.311 mmol) was added cesium carbonate (0.203 g, 0.622 mmol) and the reaction mixture was stirred at 80 C for 5 hours. The reaction mixture was cooled to ambient temperature, diluted with water (15 mE) and stirred for 10 minutes. The reaction mixture was extracted with EtOAc and the combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified over silica gel (50% EtOAc/hexanes) to afford two isomers. Faster eluting peak: trans-methyl 3-(4-(4-(1-(pentan- 3 -yl)- 1 H-pyrazol-4-yl)pyrazolo [1 ,5-ajpyrazin-6-yl)- I H-pyrazol- 1 -yl)cyclobutanecarboxylate(28 mg, 21% yield) as an off-white foam. Slower eluting peak: cis-methyl 3-(4-(4-(1-(pentan- 3-yl)-l H-pyrazol-4-yl)pyrazolo [1 ,5-a]pyrazin-6-yl)- 1 H-pyrazol- 1 -yl)cyclobutanecarboxylate(58mg, 43% yield) as a thick oil.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 3-chlorocyclobutanecarboxylate, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; ARRAY BIOPHARMA INC.; CELGENE CORPORATION; ALLEN, Shelley; BOYS, Mark Laurence; CHICARELLI, Mark J.; FELL, Jay Bradford; FISCHER, John P.; GAUDINO, John; HICKEN, Erik James; HINKLIN, Ronald Jay; KRASER, Christopher F.; LAIRD, Ellen; ROBINSON, John E.; TANG, Tony P.; BURGESS, Laurence E.; RIEGER, Robert Andrew; PHENEGER, Jed; SATOH, Yoshitaka; LEFTHERIS, Katerina; RAHEJA, Raj K.; BENNETT, Brydon L.; (223 pag.)WO2016/90285; (2016); A1;,
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