Lamifiban

Base Information

• Chemical Name: Lamifiban
• CAS No.: 144412-49-7
• Molecular Formula: C24H28 N4 O6
• Molecular Weight: 468.51
• UNII: 9XOE28082S
• DSSTox Substance ID: DTXSID20869939
• Nikkaji Number: J525.653D
• Wikidata: Q27273359
• NCI Thesaurus Code: C83862
• ChEMBL ID: CHEMBL108111
• Mol file: 144412-49-7.mol

Synonyms:((1-(N-(p-(amidinobenzoyl)tyrosyl)-4-piperidinyl)oxy))acetic acid;lamifiban;Ro 44-9883;Ro 449883;Ro-44-9883

Chemical Property of Lamifiban

Chemical Property:

• Melting Point: above 200° (dec)
• Boiling Point: °Cat760mmHg
• PKA: 3.42±0.10(Predicted)
• Flash Point: °C
• PSA: 166.04000
• Density: 1.39g/cm³
• LogP: 2.23840
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 468.20088463
• Heavy Atom Count: 34
• Complexity: 723

Purity/Quality:

97% ^*data from raw suppliers

LAMIFIBAN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCC1OCC(=O)O)C(=O)C(CC2=CC=C(C=C2)O)NC(=O)C3=CC=C(C=C3)C(=N)N
• Isomeric SMILES: C1CN(CCC1OCC(=O)O)C(=O)[C@H](CC2=CC=C(C=C2)O)NC(=O)C3=CC=C(C=C3)C(=N)N
• Uses: Antithrombotic.

Technology Process of Lamifiban

There total 14 articles about Lamifiban 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: 43.0%

{1-[2-[4-(N-hydroxycarbamimidoyl)-benzoylamino]-3-(4-hydroxy-phenyl)-propionyl]-piperidin-4-yloxy}-acetic acid (351184-45-7) → lamifiban (144412-49-7)

Guidance literature:

With hydrogen; acetic anhydride; acetic acid; palladium on activated charcoal;

DOI:10.1002/jccs.200100024

Reference yield:

4-HYDROXYPIPERIDINE (5382-16-1) → lamifiban (144412-49-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 63 percent / triethylamine (TEA) / CH₂Cl₂ / 16 h / Ambient temperature

2: 76 percent / tetra-n-butylammonium hydrogen sulfate, aq. NaOH / CH₂Cl₂; H₂O / 16 h

3: 94 percent / H₂ / 10percent Pd/C / ethanol / 3 h / 760 Torr

4: 1.)2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT), N-methylmorpholine (NMM), 2.) N-methylmorpholine (NMM) / 1.) CH₂Cl₂, 0 deg C, 3 h, 2.) CH₂Cl₂, RT, 12 h

5: H₂ / 10percent Pd/C / ethanol; acetic acid / 3 h / 760 Torr

6: tetra-n-butylammonium hydrogen sulfate, aq. NaHCO₃ / CH₂Cl₂ / 16 h / Ambient temperature

7: trifluoroacetic acid (TFA) / CH₂Cl₂ / 2 h / Ambient temperature

With 4-methyl-morpholine; sodium hydroxide; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; water; acetic acid;

DOI:10.1021/jm00101a017

Reference yield:

1-(benzyloxycarbonyl)-4-hydroxypiperidine (95798-23-5) → lamifiban (144412-49-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 76 percent / tetra-n-butylammonium hydrogen sulfate, aq. NaOH / CH₂Cl₂; H₂O / 16 h

2: 94 percent / H₂ / 10percent Pd/C / ethanol / 3 h / 760 Torr

3: 1.)2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT), N-methylmorpholine (NMM), 2.) N-methylmorpholine (NMM) / 1.) CH₂Cl₂, 0 deg C, 3 h, 2.) CH₂Cl₂, RT, 12 h

4: H₂ / 10percent Pd/C / ethanol; acetic acid / 3 h / 760 Torr

5: tetra-n-butylammonium hydrogen sulfate, aq. NaHCO₃ / CH₂Cl₂ / 16 h / Ambient temperature

6: trifluoroacetic acid (TFA) / CH₂Cl₂ / 2 h / Ambient temperature

With 4-methyl-morpholine; sodium hydroxide; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; water; acetic acid;

DOI:10.1021/jm00101a017

upstream raw materials:

(S)-<<1-<2-<4-<(aminoiminomethyl)benzoyl>amino>-3-(4-hydroxyphenyl)propionyl>piperidin-4-yl>oxy>acetic acid tert-butyl ester

{1-[2-[4-(N-hydroxycarbamimidoyl)-benzoylamino]-3-(4-hydroxy-phenyl)-propionyl]-piperidin-4-yloxy}-acetic acid

4-cyano-N-[1-(4-hydroxy-benzyl)-2-(4-hydroxy-piperidin-1-yl)-2-oxo-ethyl]-benzamide

{1-[3-(4-tert-butoxy-phenyl)-2-(4-cyano-benzoylamino)-propionyl]-piperidin-4-yloxy}-acetic acid tert-butyl ester

Downstream raw materials:

{1-[(S)-2-(4-{Amino-[(Z)-ethoxycarbonylimino]-methyl}-benzoylamino)-3-(4-hydroxy-phenyl)-propionyl]-piperidin-4-yloxy}-acetic acid isopropyl ester

Refernces

• 1、 Alig,Edenhofer,Hadvary,Hurzeler,Knopp,Muller,Steiner,Trzeciak,Weller. "Low molecular weight, non-peptide fibrinogen receptor antagonists". . p. 4393 - 4407. Retrieved 2007/10/02.