N,N'-Bis-Z-1-guanylpyrazole

Base Information

• Chemical Name: N,N'-Bis-Z-1-guanylpyrazole
• CAS No.: 152120-55-3
• Molecular Formula: C20H18N4O4
• Molecular Weight: 378.387
• Hs Code.: 29331990
• European Community (EC) Number: 628-402-7
• DSSTox Substance ID: DTXSID20422902
• Mol file: 152120-55-3.mol

Synonyms:N,N'-BIS-Z-1-GUANYLPYRAZOLE;152120-55-3;N,N'-Bis(benzyloxycarbonyl)-1H-pyrazole-1-carboxamidine;Benzyl ((((benzyloxy)carbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate;benzyl (NZ)-N-[phenylmethoxycarbonylamino(pyrazol-1-yl)methylidene]carbamate;N,N'-Bis(carbobenzoxy)-1H-pyrazole-1-carboxamidine;N,N-BISBENZYLOXYCARBONYL-1-GUANYLPYRAZOLE;N,N'-Bs-Z-1-guanylpyrazole;SCHEMBL670164;DTXSID20422902;N,N'-Di-Cbz-1H-pyrazole-1-carbo;1-[N,N'-(Di-Cbz)amidino]pyrazole;MFCD02092983;AKOS007930853;AKOS025117323;AM84479;CS-W008067;N,N/'-BIS-Z-1-GUANYLPYRAZOLE;AS-11122;N,N'-Di-Cbz-1H-pyrazole-1-carboxamidine;1-[N,N'-Bis(carbobenzoxy)amidino]pyrazole;B3605;A809261;J-008886;J-523221;N,N'-Bis(carbobenzoxy)-1H-pyrazole-1-carboximidamide;N,N\'-Bis(benzyloxycarbonyl)-1H-pyrazole-1-carboxamidine;benzyl ((benzyloxycarbonylamino)(1h-pyrazol-1-yl)methylene)carbamate;Benzyl ((((benzyloxy)carbonyl)amino)-(1H-pyrazol-1-yl)methylene)carbamate

Chemical Property of N,N'-Bis-Z-1-guanylpyrazole

Chemical Property:

• Melting Point: 90-96 °C
• PKA: 6.66±0.46(Predicted)
• PSA: 94.81000
• Density: 1.25 g/cm³
• LogP: 3.74130
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 378.13280507
• Heavy Atom Count: 28
• Complexity: 542

Purity/Quality:

99% ^*data from raw suppliers

N,N''-Bis-Z-1-Guanylpyrazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(=NC(=O)OCC2=CC=CC=C2)N3C=CC=N3
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)N/C(=N/C(=O)OCC2=CC=CC=C2)/N3C=CC=N3
• Uses: N,N'-Bis(benzyloxycarbonyl)-1H-pyrazole-1-carboxamidine is used as pharmaceutical intermediate.

Technology Process of N,N'-Bis-Z-1-guanylpyrazole

There total 4 articles about N,N'-Bis-Z-1-guanylpyrazole 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: 75.0%

N-benzyloxycarbonyl-1H-pyrrazole-1-carboxamidine (152120-62-2) + benzyl chloroformate (501-53-1,94274-21-2) → N,N-bis(benzyloxycarbonyl)-1H-pyrazole-1-carboxamidine (152120-55-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 2.5h;

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → N,N-bis(benzyloxycarbonyl)-1H-pyrazole-1-carboxamidine (152120-55-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / DIEA / dimethylformamide / 0.67 h / 0 °C

2: 1.) NaH / 1.) THF, 0 deg C, 5 min, 2.) THF, RT, 1.5 h

With sodium hydride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;

DOI:10.1080/00397919308011149

Reference yield:

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + (N)-benzyloxycarbonyl-1H-pyrazole-1-carboxamidine (152120-62-2) → N,N-bis(benzyloxycarbonyl)-1H-pyrazole-1-carboxamidine (152120-55-3)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) THF, 4 deg C, 2.) room temperature;

DOI:10.1016/S0040-4039(00)79163-5

upstream raw materials:

N-(Benzyloxycarbonyloxy)succinimide

(N)-benzyloxycarbonyl-1H-pyrazole-1-carboxamidine

N-(benzyloxycarbonyl)succinimide

benzyl chloroformate

Downstream raw materials:

N^α-(N,N'-bis-benzyloxycarbonyl)amidino-Tyr(Me)-D-Pro-OH

C₃₂H₃₄N₄O₈

C₃₇H₄₉N₅O₉

C₃₇H₄₉N₅O₉

Refernces

• 1、 Bernatowicz, Michael S.,Wu, Youling,Matsueda, Gary R.. "Urethane protected derivatives of 1-guanylpyrazole for the mild and efficient preparation of guanidines". . p. 3389 - 3392. Retrieved 2007/10/02.