Famotidine cyanoamidine

Base Information

• Chemical Name: Famotidine cyanoamidine
• CAS No.: 76823-97-7
• Molecular Formula: C₉H₁₃N₇S₂
• Molecular Weight: 283.381
• UNII: 0S6W675X8H
• ChEMBL ID: CHEMBL171370
• DSSTox Substance ID: DTXSID50227644
• Nikkaji Number: J679.059C
• Wikidata: Q27237179
• Mol file: 76823-97-7.mol

Synonyms:Famotidine cyanoamidine;76823-97-7;Famotidine Impurity G;N-Desaminosulfonyl-N-cyano Famotidine;0S6W675X8H;N'-cyano-3-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]propanimidamide;N-Cyano-3-(((2-((diaminomethylidene)amino)thiazol-4-yl)methyl)sulfanyl)propanimidamide;Propanimidamide, 3-(((2-((aminoiminomethyl)amino)-4-thiazolyl)methyl)thio)-N-cyano-;N-Cyano-3-(((2-guanidinothiazol-4-yl)methyl)thio)propanimidamide;Famotidine impurity G [EP];UNII-0S6W675X8H;Famotidine specified impurity G [EP];CHEMBL171370;SCHEMBL11241172;SCHEMBL23804921;DTXSID50227644;DFHYHFAHYAJKDU-UHFFFAOYSA-N;FAMOTIDINE IMPURITY G [EP IMPURITY];Q27237179;N-cyano-3-[(2-guanidinothiazol-4-yl)-methylthio]propionamidine;N-cyano-3-[(2-guanidinothiazol-4-yl)methylthio]propionamidine

Chemical Property of Famotidine cyanoamidine

Chemical Property:

• Boiling Point: 461.2±55.0 °C(Predicted)
• PKA: 8.52±0.70(Predicted)
• Density: 1.58±0.1 g/cm3(Predicted)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 283.06738579
• Heavy Atom Count: 18
• Complexity: 368

Purity/Quality:

99.90% ^*data from raw suppliers

N-Desaminosulfonyl-N-cyanoFamotidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(N=C(S1)N=C(N)N)CSCCC(=NC#N)N
• Uses: An impurity of Famotidine (F102250).

Technology Process of Famotidine cyanoamidine

There total 6 articles about Famotidine cyanoamidine 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: 70.7%

CYANAMID (420-04-2) + methyl 3-<<<2-<(diaminomethylene)amino>-4-thiazolyl>methyl>thio>propionimidate (76823-94-4) → 3-<<<2-<(diaminomethylene)amino>-4-thiazolyl>methyl>thio>-N'-cyanopropionamidine (76823-97-7)

Guidance literature:

In methanol; for 0.5h; Ambient temperature;

DOI:10.1021/jm00373a007

Reference yield:

3-(2-aminothiazol-4-yl-methylthio)propionitrile (76823-89-7) → 3-<<<2-<(diaminomethylene)amino>-4-thiazolyl>methyl>thio>-N'-cyanopropionamidine (76823-97-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 87.3 percent / acetone / 5 h / Heating

2: 93.5 percent / aq. K₂CO₃ / acetone; methanol / 5 h / 50 °C

3: 89.9 percent / ethanol / 1 h / Heating

4: 51.45 percent / ammonia, NH₄Cl / methanol / 15 h / 80 - 90 °C

5: 81.8 percent / HCl / dimethylformamide / 48 h / 4 °C

6: 70.7 percent / methanol / 0.5 h / Ambient temperature

With hydrogenchloride; ammonia; potassium carbonate; ammonium chloride; In methanol; ethanol; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm00373a007

Reference yield:

N''-[4-[[(2-cyanoethyl)thio]methyl]-2-thiazolyl]-guanidine (76823-93-3) → 3-<<<2-<(diaminomethylene)amino>-4-thiazolyl>methyl>thio>-N'-cyanopropionamidine (76823-97-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 81.8 percent / HCl / dimethylformamide / 48 h / 4 °C

2: 70.7 percent / methanol / 0.5 h / Ambient temperature

With hydrogenchloride; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00373a007

upstream raw materials:

CYANAMID

methyl 3-<<<2-<(diaminomethylene)amino>-4-thiazolyl>methyl>thio>propionimidate

3-(2-aminothiazol-4-yl-methylthio)propionitrile

N''-[4-[[(2-cyanoethyl)thio]methyl]-2-thiazolyl]-guanidine

Refernces