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What is N,N'-Di-Boc-1H-pyrazole-1-carboxamidine?

Feb 19，2020

N,N'-Di-Boc-1H-pyrazole-1-carboxamidine is used in the stereoselective synthesis of the bicyclic guanidine alkaloid (+)-monanchorin[1,2].N,N'-Di-Boc-1H-pyrazole-1-carboxamidine (also known as Bis-Boc-pyrazolocarboxamidine,Pyrazol(BOC)2) is typically used as a guanidinylating reagent in organic synthesis.

Fig 1. Chemical structure formula and three-dimensional structure of N,N'-BIS-BOC-1-GUANYLPYRAZOLE

N,N'-Di-Boc-1H-pyrazole-1-carboxamidine is prepared by the initial reaction of 1 equiv of di‐tert‐butyl‐dicarbonate with 1H‐pyrazole‐1‐carboxamidine hydrochloride in the presence of diisopropylethylamine giving the mono‐Boc‐derivative. The second Boc group is then introduced by treatment with di‐tert‐butyl‐dicarbonate following deprotonation with sodium hydride. Lithium hydride may also be used as a base in the second stage.Crude product of N,N'-Di-Boc-1H-pyrazole-1-carboxamidine may be purified via silica gel chromatography or crystallization from MeOH/H2O to give a cream‐to‐white crystalline solid.It should be stored at or below −4 °C. Allow bottle to warm to room temperature prior to use. Open container with caution in a fumehood in case pressure has developed. Avoid exposure to acids in closed containers. The toxicological activity is unknown, although pyrazole is considered a possible teratogen[3,4].

Guanidine compound is a very basic organic base, and it is also the most biologically active organic base.It can be protonated in the physiological p H medium to form a positively charged group, which can form static electricity with the substrate. interaction. The nitrogen and hydrogen atoms on the guanidine group have a high affinity for carbonates, phosphates, and peptides, and it is easy to form hydrogen bonds. It is these guanidine-based compounds that produce anti-inflammatory, anti-histamine, antihypertensive, hypoglycemic, and antibacterial functions. Therefore there are two Boc, PM and two Cbz N, N′-dibenzyloxycarbonyl-1H-pyridines(PC). The reactivity of azole-1, formazan is better than that of PJ. Some amines that do not react with PJ can react with PM or PC reaction to obtain a double-protected guanidyl compound, acid-hydrolyzed The guanidyl compound is obtained afterwards, the reaction conditions are mild, and the post-treatment is easy.Using PJ as raw material, N-tert-butoxycarbonyl-1H-pyrazole-1-formamidine (PB ), The yield is as high as 80% to 95%.

References

[1]Gregory J. Gabriel.; Ahmad E. Madkour.; Jeffrey M. Dabkowski.; Christopher F. Nelson.; Klaus Nüsslein.; Gregory N. Tew. Synthetic Mimic of Antimicrobial Peptide with Nonmembrane-Disrupting Antibacterial Properties.Biomacromolecules. 2008, 9 (11),2980-2983.

[2]Luca Gentilucci.; Giuliana Cardillo.; Federico Squassabia.; Alessandra Tolomelli.; Santi Spampinato.; Antonino Sparta.; Monica Baiula. Inhibition of cancer cell adhesion by heterochiral Pro-containing RGD mimetics. Bioorg. Med. Chem. Lett. 2007, 17 (8),2329-2333.

[3]Mccabe N, Turner N C, Lord C J, et al. McCabe N, Turner NC, Lord CJ, Kluzek K, Bialkowska A, Swift S et al. Deficiency in the repair of DNA damage by homologous recombination and sensitivity to poly(ADP-ribose) polymerase inhibition. Cancer Res 66: 8109-8115[J]. 2006, 66(16):8109-8115.

[4]Caroline M. Reid, Charles Ebikeme, Michael P. Barrett,等. Synthesis of novel benzamidine- and guanidine-derived polyazamacrocycles: Selective anti-protozoal activity for human African trypanosomiasis[J]. 18(20):5399-5401.

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