Famotidine propanamide

Base Information

• Chemical Name: Famotidine propanamide
• CAS No.: 76824-16-3
• Molecular Formula: C8H13N5OS2
• Molecular Weight: 259.35200
• Hs Code.: 2934990002
• UNII: 4TT820HMTW
• ChEMBL ID: CHEMBL169288
• Nikkaji Number: J524.592C
• Wikidata: Q27260482
• Mol file: 76824-16-3.mol

Synonyms:Famotidine propanamide;Famotidine Impurity D;4TT820HMTW;UNII-4TT820HMTW;Famotidine impurity D [EP];3-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]propanamide;Famotidine specified impurity D [EP];3-(((2-((Diaminomethylidene)amino)thiazol-4-yl)methyl)sulfanyl)propanamide-;Propanamide, 3-(((2-((aminoiminomethyl)amino)-4-thiazolyl)methyl)thio)-;3-(((2-guanidinothiazol-4-yl)methyl)thio)propanimidic acid;CHEMBL169288;SCHEMBL9817418;SCHEMBL18335715;BLXXXPVCYVHTQA-UHFFFAOYSA-N;3-[[[2-[(Aminoiminomethyl)amino]-4-thiazolyl]methyl]thio]propanamide;FAMOTIDINE IMPURITY D [EP IMPURITY];3-(2-guanidinothiazol-4-ylmethylthio)propionamide;Q27260482;3-[[[2-[(diaminomethylene)amino]thiazol-4-yl]methyl]thio]propanamide

Chemical Property of Famotidine propanamide

Chemical Property:

• Melting Point: >140°C (dec.)
• Boiling Point: 530.5±60.0 °C(Predicted)
• PKA: 16.19±0.40(Predicted)
• PSA: 172.41000
• Density: 1.63±0.1 g/cm3(Predicted)
• LogP: 2.57980
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly, Heated, Soni
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 259.05615240
• Heavy Atom Count: 16
• Complexity: 269

Purity/Quality:

98%Min ^*data from raw suppliers

3-[[[2-[(Aminoiminomethyl)amino]-4-thiazolyl]methyl]thio]propanamide ^*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(=O)N
• Uses: Famotidine impurity.

Technology Process of Famotidine propanamide

There total 7 articles about Famotidine propanamide 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: 67.5%

methyl 3-<<<2-<(diaminomethylene)amino>-4-thiazolyl>methyl>thio>propionimidate (76823-94-4) → 3-<2-(diaminomethyleneamino)-4-thiazolylmethylthio>-propionamide (76824-16-3)

Guidance literature:

With water; In ethanol; at 40 ℃; for 20h;

DOI:10.1021/jm00373a007

Reference yield:

famotidine (76824-35-6) → 3-<2-(diaminomethyleneamino)-4-thiazolylmethylthio>-propionamide (76824-16-3) + 3-<<<2-<(diaminomethylene)amino>-4-thiazolyl>methyl>thio>propionic acid (107880-74-0) + N-(aminosulphonyl)-3-[[[2-[(diaminomethylene)amino]thiazol-4-l]methyl]thio]propanamide

Guidance literature:

With Soersen buffer; In methanol; at 55 ℃; pH=1.71; Further Variations:; Temperatures; pH-values; Kinetics;

DOI:10.1023/A:1016222501079

Reference yield:

3-(2-aminothiazol-4-yl-methylthio)propionitrile (76823-89-7) → 3-<2-(diaminomethyleneamino)-4-thiazolylmethylthio>-propionamide (76824-16-3)

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: 67.5 percent / water / ethanol / 20 h / 40 °C

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

DOI:10.1021/jm00373a007

upstream raw materials:

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

famotidine

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

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

Refernces

• 1、 Yanagisawa,Hirata,Ishii. "Histamine H2 receptor antagonists. 1. Synthesis of N-cyano and N-carbamoyl amidine derivatives and their biological activities.". . p. 849 - 857. Retrieved 2007/10/02.