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tert-Butyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate

  • CAS No. 398491-59-3

  • Cat. No. CS-W004901
  • Purity≥98%
  • MDL No.MFCD08275050

*For research and further manufacturing use only, not for direct human use.

tert-Butyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate|CS-W004901

Structure of 398491-59-3

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General Information

  • CAS No. 398491-59-3
  • Cat. No. CS-W004901
  • Purity ≥98%
  • MDL No. MFCD08275050
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₆N₄O₂
  • Molecular Weight 224.26
  • Synonym(s) 2-Methyl-2-propanyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate
  • SMILES O=C(N(C1)CC2=C1C(N)=NN2)OC(C)(C)C

Description

tert-Butyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate is a bench-stable heterocyclic building block featuring a reducible pyrazole core and a protected amine. This scaffold integrates seamlessly into medicinal chemistry campaigns targeting kinase inhibitors and CNS-active agents, offering enhanced solubility and metabolic stability in synthetic routes.

Application

tert-Butyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate serves as a versatile heterocyclic building block for medicinal chemistry and process development. The dihydropyrrolopyrazole core enables efficient functionalization at the C3-amino and C5-carboxylate positions, with the tert-butyl ester offering excellent bench stability and straightforward deprotection under mild acidic conditions. Its compatibility with standard coupling reactions and tolerance to diverse functional groups support reliable integration into complex molecular architectures.

Synthesis

  • Route1

    References

    • Fancelli, Daniele; Berta, Daniela; Bindi, Simona; Cameron, Alexander; Cappella, Paolo; Carpinelli, Patrizia; Catana, Cornel; Forte, Barbara; Giordano, Patrizia; Giorgini, Maria Laura; Mantegani, Sergio; Marsiglio, Aurelio; Meroni, Maurizio; Moll, Juergen; Pittala, Valeria; Roletto, Fulvia; Severino, Dino; Soncini, Chiara; Storici, Paola; Tonani, Roberto; Varasi, Mario; Vulpetti, Anna; Vianello, Paola Journal of Medicinal Chemistry, 2005 , vol. 48, # 8 p. 3080 - 3084
  • Route2
    • Methyl 2-{[(tert-butoxy)carbonyl](2-cyanoethyl)aminoacetate|CS-0757087
      266353-19-9
    • ~%
    • In-stock
      tert-Butyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate|CS-W004901
      398491-59-3

    References

    • Fancelli, Daniele; Berta, Daniela; Bindi, Simona; Cameron, Alexander; Cappella, Paolo; Carpinelli, Patrizia; Catana, Cornel; Forte, Barbara; Giordano, Patrizia; Giorgini, Maria Laura; Mantegani, Sergio; Marsiglio, Aurelio; Meroni, Maurizio; Moll, Juergen; Pittala, Valeria; Roletto, Fulvia; Severino, Dino; Soncini, Chiara; Storici, Paola; Tonani, Roberto; Varasi, Mario; Vulpetti, Anna; Vianello, Paola Journal of Medicinal Chemistry, 2005 , vol. 48, # 8 p. 3080 - 3084
  • Route3
    • N-(2-Cyanoethyl)glycine|CS-0201685
      3088-42-4
    • ~%
    • In-stock
      tert-Butyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate|CS-W004901
      398491-59-3

    References

    • Fancelli, Daniele; Berta, Daniela; Bindi, Simona; Cameron, Alexander; Cappella, Paolo; Carpinelli, Patrizia; Catana, Cornel; Forte, Barbara; Giordano, Patrizia; Giorgini, Maria Laura; Mantegani, Sergio; Marsiglio, Aurelio; Meroni, Maurizio; Moll, Juergen; Pittala, Valeria; Roletto, Fulvia; Severino, Dino; Soncini, Chiara; Storici, Paola; Tonani, Roberto; Varasi, Mario; Vulpetti, Anna; Vianello, Paola Journal of Medicinal Chemistry, 2005 , vol. 48, # 8 p. 3080 - 3084

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   84.24
  • LogP   1.2426
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   0

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