5-tert-Butyl 1-ethyl 3-aminopyrrolo[3,4-c]pyrazole-1,5(4H,6H)-dicarboxylate

Base Information

• Chemical Name: 5-tert-Butyl 1-ethyl 3-aminopyrrolo[3,4-c]pyrazole-1,5(4H,6H)-dicarboxylate
• CAS No.: 398495-65-3
• Molecular Formula: C13H20 N4 O4
• Molecular Weight: 296.326
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID10426095
• Wikidata: Q72477245
• Mol file: 398495-65-3.mol

Synonyms:398495-65-3;5-tert-Butyl 1-ethyl 3-aminopyrrolo[3,4-c]pyrazole-1,5(4H,6H)-dicarboxylate;5-Boc-3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-1-carboxylic acid ethyl ester;1-ETHYLOXYCARBONYL-5-BOC-3-AMINO-4,6-DIHYDRO-PYRROLO[3,4-C]PYRAZOLE;3-Amino-4,6-dihydro-pyrrolo[3,4-c]pyrazole-1,5-dicarboxylic acid 5-tert-butyl ester 1-ethyl ester;5-O-tert-butyl 1-O-ethyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate;MFCD08061258;5-(tert-butyl) 1-ethyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate;5-Boc-3-amino-4,6-dihydropyrrolo[3,4-c]-pyrazole-1-carboxylic acid ethyl ester;5-tert-butyl 1-ethyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate;SCHEMBL1370694;DTXSID10426095;VUWAGENLXQIUJY-UHFFFAOYSA-N;AMY15299;AKOS015838691;SB17798;AS-37692;SY110943;CS-0088966;FT-0646181;4-(2-HYDROXYETHOXY)BENZOICACIDMETHYLESTER;5-tert-Butyl1-ethyl3-aminopyrrolo[3,4-c]pyrazole-1,5(4H,6H)-dicarboxylate;Ethyl 5-Boc-3-amino-5,6-dihydropyrrolo[3,4-c]pyrazole-1(4H)-carboxylate;3-amino-5-tert-butyloxycarbonyl-1-ethoxycarbonyl-4,6-dihydropyrrolo[3,4-c]pyrazole;5-tert-butyloxycarbonyl-1-ethoxycarbonyl-3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole

Chemical Property of 5-tert-Butyl 1-ethyl 3-aminopyrrolo[3,4-c]pyrazole-1,5(4H,6H)-dicarboxylate

Chemical Property:

• Boiling Point: 453.4±55.0 °C(Predicted)
• PKA: 2.44±0.20(Predicted)
• PSA: 99.68000
• Density: 1.36
• LogP: 2.23970
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 296.14845513
• Heavy Atom Count: 21
• Complexity: 423

Purity/Quality:

97% ^*data from raw suppliers

5-Boc-3-amino-4,6-dihydropyrrolo[3,4-c]-pyrazole-1-carboxylic acid ethyl ester 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)N1C2=C(CN(C2)C(=O)OC(C)(C)C)C(=N1)N

Technology Process of 5-tert-Butyl 1-ethyl 3-aminopyrrolo[3,4-c]pyrazole-1,5(4H,6H)-dicarboxylate

There total 9 articles about 5-tert-Butyl 1-ethyl 3-aminopyrrolo[3,4-c]pyrazole-1,5(4H,6H)-dicarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

3-amino-4,6-dihydro-1H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester (398491-59-3) + chloroformic acid ethyl ester (541-41-3) → 3-amino-4,6-dihydro-pyrrolo[3,4-c]pyrazole-1,5-dicarboxylic acid 5-tert-butyl ester 1-ethyl ester (398495-65-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/jm049076m

Reference yield:

ethyl hydrazinecarboxylate hydrochloride (25544-75-6) + 3-cyano-4-oxopyrrolidine-1-carboxylic acid tert-butyl ester (175463-32-8) → 3-amino-4,6-dihydro-pyrrolo[3,4-c]pyrazole-1,5-dicarboxylic acid 5-tert-butyl ester 1-ethyl ester (398495-65-3)

Guidance literature:

In ethanol; at 60 ℃;

Reference yield:

N-(2-cyanoethyl)glycine (3088-42-4) → 3-amino-4,6-dihydro-pyrrolo[3,4-c]pyrazole-1,5-dicarboxylic acid 5-tert-butyl ester 1-ethyl ester (398495-65-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: H₂SO₄ / 7 h / Heating

2.1: 88 percent / aq. NaHCO₃ / CH₂Cl₂ / 24 h / 22 °C

3.1: MeONa / toluene / 3 h / 80 °C

3.2: 83 percent / aq. HCl / 2 h / 22 °C

4.1: 31 percent / hydrazine dihydrochloride / ethanol / 3 h / 60 °C

5.1: 72 percent / DIEA / tetrahydrofuran / 0 - 20 °C

With hydrazine dihydrochloride; sulfuric acid; sodium methylate; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1021/jm049076m

upstream raw materials:

3-amino-4,6-dihydro-1H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester

chloroformic acid ethyl ester

[tert-butoxycarbonyl-(2-cyanoethyl)amino]acetic acid methyl ester

N-(2-cyanoethyl)glycine

Downstream raw materials:

C₂₈H₃₀N₄O₈

C₂₂H₂₈N₄O₇

tert-butyl 3-(4-methoxybenzamido)pyrrolo[3,4-c]pyrazole-5(1H,4H,6H)-carboxylate

tert-butyl 3-(2-phenylacetamido)pyrrolo[3,4-c]pyrazole-5(1H,4H,6H)-carboxylate