Mosapride

Base Information

• Chemical Name: Mosapride
• CAS No.: 112885-41-3
• Deprecated CAS: 144256-27-9
• Molecular Formula: C21H25ClFN3O3
• Molecular Weight: 421.899
• Hs Code.: 2934999090
• European Community (EC) Number: 601-210-0
• UNII: I8MFJ1C0BY
• DSSTox Substance ID: DTXSID2048408
• Nikkaji Number: J245.710E
• Wikipedia: Mosapride
• Wikidata: Q68566
• NCI Thesaurus Code: C66204
• Pharos Ligand ID: ZMD1L83552B1
• Metabolomics Workbench ID: 152792
• ChEMBL ID: CHEMBL60889
• Mol file: 112885-41-3.mol

Synonyms:4-amino-5-chloro-2-ethoxy-N-((4-(4-fluorobenzyl)-2-morpholinyl)methyl)benzamide;AS 4370;AS-4370;mosapride;mosapride citrate;Mosapride UI05MSP015CT

Chemical Property of Mosapride

Chemical Property:

• Appearance/Colour: White to off-white crystalline solid
• Vapor Pressure: 4.11E-12mmHg at 25°C
• Melting Point: 151-153 °C
• Refractive Index: 1.584
• Boiling Point: 549.211 °C at 760 mmHg
• PKA: 13.52±0.46(Predicted)
• Flash Point: 285.953 °C
• PSA: 76.82000
• Density: 1.272 g/cm³
• LogP: 4.00080
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 421.1568475
• Heavy Atom Count: 29
• Complexity: 521

Purity/Quality:

99% ^*data from raw suppliers

Mosapride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,N,F+
• Hazard Codes: C,N,F+

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC1=CC(=C(C=C1C(=O)NCC2CN(CCO2)CC3=CC=C(C=C3)F)Cl)N
• Recent ClinicalTrials: Efficacy of Mosapride on Recovery of Intestinal Motility After Elective Colorectal Cancer Surgery
• Recent NIPH Clinical Trials: The comparison on effectiveness between mopride and acotiamide in the functional dyspepsia patients
• Description: Mosapride citrate, a new gastroprokinetic benzamide was introduced in Japan as Gasmotin for the relief of gastrointestinal symptoms in patients with chronic gastritis, gastro-oesophageal reflux, dyspepsia and post-surgery use. Mosapride is synthesized by final amidation between the corresponding benzoic acid, itself obtained in 3 steps from methyl 4-acetamido salicylate, and the appropriate 2-aminomethyl-morpholine. Mosapride is a 5-HT4 partial agonist without notable activity for D2, 5-HT1 , 5-HT2, alpha-1 and alpha-2 receptors. In dogs, mosapride was as potent as cisapride to stimulate antral and duodenal motility. In most of species including man, mosapride undergoes extensive cleavage to a N-debenzylated metabolite which retains partial 5-HT4 activity but has potent 5-HT3 antagonist activity.
• Uses: A selective 5-HT4 receptor agonist. Gastroprokinetic. gastroprokinetic agent

Technology Process of Mosapride

There total 20 articles about Mosapride 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: 100.0%

(RS)-4-(tert-butoxy-carbonyl-amino)-5-chloro-2-ethoxy-N-{[4-(4-fluoro-benzyl)-2-morpholinyl]methyl}-benzamide (636582-70-2) → mosapride (112885-41-3)

Guidance literature:

With hydrogenchloride; In water; at 40 ℃; for 3h; Alkaline aqueous solution;

Reference yield: 96.5%

C21H23ClFN3O5 → mosapride (112885-41-3)

Guidance literature:

With iron; ammonium chloride; In ethanol; water; for 5h; Reagent/catalyst; Solvent; Reflux;

Reference yield: 74.0%

2-ethoxy-4-amino-5-chlorobenzyl methyl ether + 2-aminomethyl-4-(4-fluoro-benzyl) morpholine (112914-13-3) → mosapride (112885-41-3)

Guidance literature:

With di-tert-butyl peroxide; iodine; In acetonitrile; at 70 ℃; for 8h;

upstream raw materials:

4-amino-5-chloro-2-ethoxybenzoic acid

2-aminomethyl-4-(4-fluoro-benzyl) morpholine

methyl 4-acetamido-2-hydroxybenzoate

4-Acetylamino-5-chloro-2-ethoxy-benzoic acid methyl ester

Downstream raw materials:

4-amino-2-ethoxy-N-(2-morpholinylmethyl)benzamide

mosapride citrate

4-Amino-5-chloro-N-[4-(4-fluoro-benzyl)-morpholin-2-ylmethyl]-2-(3-methyl-but-2-enyloxy)-benzamide

4-Amino-5-chloro-N-[4-(4-fluoro-benzyl)-morpholin-2-ylmethyl]-2-(3-methyl-butoxy)-benzamide

Refernces

• 1、 -. "Synthesis method of mosapride citrate". Paragraph 0046; 0047. . Retrieved 2020/07/15.
• 2、 -. "DRY-COATED ORALLY-DISINTEGRATING TABLET". . . Retrieved 2012/03/27.