Synthesis and Chemistry of 5,6,7,8-Tetrahydro-4H-Pyrazolo[1,5-a] [1,4]Diazepine-2-Carboxylates.

02 November 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a] diazepine carboxylates are valuable scaffolds for drug design and medicinal chemistry. In this paper we disclose a short scalable synthesis and chemical reactivity patterns of the pyrazolo-diazepine pharmacophore. Commercial and cheaply available Methyl pyrazole 3,5-dicarboxylate was alkylated with 3-bromo-N-Boc propyl amine and the resulting derivative underwent concomitant cyclization upon deprotection of the Boc protecting group to yield the pyrazolo-diazepine skeleton. Selective reduction of the lactam was accomplished cleanly using borane and the resulting amine was pro-tected using a tert-butyloxycarbonyl protecting group. The free N-terminal of the diazepine underwent smooth Buchwald and Chan arylations among various standard chemistry applications examined on this pharmacophore.


Kinase inhibitor
pyrazolo diazepines


Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.