Lafutidine

Base Information

• Chemical Name: Lafutidine
• CAS No.: 206449-93-6
• Deprecated CAS: 143375-16-0
• Molecular Formula: C22H29N3O4S
• Molecular Weight: 431.55
• UNII: 49S4O7ADLC
• ChEMBL ID: CHEMBL1742461
• DSSTox Substance ID: DTXSID0046434
• Metabolomics Workbench ID: 153697
• NCI Thesaurus Code: C79117
• Nikkaji Number: J485.641D
• Wikidata: Q582556
• Wikipedia: Lafutidine
• Mol file: 206449-93-6.mol

Synonyms:FRG 8813;FRG-8813;lafutidine;N-(4-(4-piperidinylmethyl)pyridyl-2-oxy)-(Z)-butenyl-2-(furfurylsulfinyl)acetamide;N-(4-(4-piperidinylmethyl)pyridyl-2-oxy)butenyl-2-(furfurylsulfinyl)acetamide

Chemical Property of Lafutidine

Chemical Property:

• Melting Point: 94-99°C
• Boiling Point: 704.2±60.0 °C(Predicted)
• PKA: 13.13±0.46(Predicted)
• PSA: 107.37000
• Density: 1.252
• LogP: 4.30450
• Storage Temp.: Amber Vial, -20?C Freezer
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly), Methanol (Sl
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 431.18787759
• Heavy Atom Count: 30
• Complexity: 569

Purity/Quality:

98%Min ^*data from raw suppliers

racLafutidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN(CC1)CC2=CC(=NC=C2)OCC=CCNC(=O)CS(=O)CC3=CC=CO3
• Isomeric SMILES: C1CCN(CC1)CC2=CC(=NC=C2)OC/C=C\CNC(=O)CS(=O)CC3=CC=CO3
• Recent ClinicalTrials: A Multi-center, Randomized, Double-blind Phase III Clinical Trial to Assess and Compare to the Efficacy and Safety of Lafutidine, Famotidine and Omeprazole-referenced in Korean Erosive Esophagitis Patients
• Recent NIPH Clinical Trials: Phase 2 study of dose-dense nab-paclitaxel followed by EC as neoadjuvant chemotherapy for HER2-negative breast cancer
• Uses: rac Lafutidine is a second generation histamine H2-receptor antagonist. Lafutidine is used as an antiulcerative. Second generation histamine H2-receptor antagonist. Antiulcerative.

Technology Process of Lafutidine

There total 23 articles about Lafutidine 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: 94.6%

(2Z)-4-({4-[(piperidin-1-yl)methyl]pyridin-2-yl}oxy)but-2-en-1-amine + p-nitrophenyl 2-(furfurylsulfinyl)acetate (123855-55-0) → lafutidine (118288-08-7,206449-93-6,206449-94-7)

Guidance literature:

In dichloromethane; at 25 - 30 ℃;

Reference yield:

2-Bromo-4-[1,3]dioxolan-2-yl-pyridine (118289-18-2) → lafutidine (118288-08-7,206449-93-6,206449-94-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 87 percent / NaOH, K₂CO₃, n-Bu₄NHSO₄ / toluene / 18 h / Ambient temperature

2: 90 percent / pyridinium p-toluenesulfonate, ethanol / 18 h / 55 °C

3: SOCl₂, Et₃N / CH₂Cl₂ / 1 h / 0 °C

4: n-Bu₄NHSO₄ / acetonitrile / 18 h / Heating

5: 78 percent / NH₂NH₂*H₂O / methanol / 10 h / Heating

6: 91 percent / tetrahydrofuran / 18 h / Ambient temperature

7: 52 percent / p-TsOH, H₂O / acetone / 18 h / Heating

8: 2.) NaBH₄ / 1.) EtOH, 3 h, 2.) EtOH, 16 h

With sodium hydroxide; sodium tetrahydroborate; thionyl chloride; ethanol; water; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; potassium carbonate; toluene-4-sulfonic acid; hydrazine hydrate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; acetonitrile;

DOI:10.1248/cpb.46.616

Reference yield:

(Z)-4-(4-[1,3]Dioxolan-2-yl-pyridin-2-yloxy)-but-2-enylamine (118289-22-8) → lafutidine (118288-08-7,206449-93-6,206449-94-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / tetrahydrofuran / 18 h / Ambient temperature

2: 52 percent / p-TsOH, H₂O / acetone / 18 h / Heating

3: 2.) NaBH₄ / 1.) EtOH, 3 h, 2.) EtOH, 16 h

With sodium tetrahydroborate; water; toluene-4-sulfonic acid; In tetrahydrofuran; acetone;

DOI:10.1248/cpb.46.616

upstream raw materials:

piperidine

N-[(Z)-4-(4-Formyl-pyridin-2-yloxy)-but-2-enyl]-2-(furan-2-ylmethanesulfinyl)-acetamide

2-Bromo-4-[1,3]dioxolan-2-yl-pyridine

(Z)-4-(4-[1,3]Dioxolan-2-yl-pyridin-2-yloxy)-but-2-enylamine