Darifenacin hydrobromide

Base Information

• Chemical Name: Darifenacin hydrobromide
• CAS No.: 133099-07-7
• Molecular Formula: C28H30N2O2^.HBr
• Molecular Weight: 507.47
• Hs Code.: 2934990002
• European Community (EC) Number: 603-705-7
• UNII: CR02EYQ8GV
• DSSTox Substance ID: DTXSID9046780
• Wikidata: Q27114313
• NCI Thesaurus Code: C78068
• RXCUI: 485417
• ChEMBL ID: CHEMBL1200935
• Mol file: 133099-07-7.mol

Synonyms:(S)-1-(2-(2,3-dihydro-5-benzofuranyl)ethyl)-alpha,alpha-diphenyl-3-pyrrolidineacetamide;darifenacin;darifenacin hydrobromide;darifenacin hydrochloride;darifenacine;darifenicin;Emselex;Enablex;UK-88525

Chemical Property of Darifenacin hydrobromide

Chemical Property:

• Vapor Pressure: 1.11E-16mmHg at 25°C
• Melting Point: 228-230 °C
• Boiling Point: 614.3 °C at 760 mmHg
• Flash Point: 325.3 °C
• PSA: 41.57000
• LogP: 5.94630
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: soluble20mg/mL, clear
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 506.15689
• Heavy Atom Count: 33
• Complexity: 607

Purity/Quality:

99% ^*data from raw suppliers

Darifenacin HBr ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CC1C(C2=CC=CC=C2)(C3=CC=CC=C3)C(=O)N)CCC4=CC5=C(C=C4)OCC5.Br
• Isomeric SMILES: C1CN(C[C@@H]1C(C2=CC=CC=C2)(C3=CC=CC=C3)C(=O)N)CCC4=CC5=C(C=C4)OCC5.Br
• Description: Darifenacin, an orally active, once a day selective M3 receptor antagonist, was launched for the treatment of overactive bladder in patients with symptoms of urge urinary incontinence, urgency and frequency. The drug selectively inhibits M3 receptor in the detrusor muscle while sparing the M1 and M2 receptors that are believed to be involved in central nervous system and cardiovascular function respectively. The compound was originally developed by Pfizer and licensed to Novartis and Bayer. Darifenacin is an antagonist of M3 muscarinic acetylcholine receptors (mAChRs; Ki = 0.76 nM). It is selective for M3 over M1, M2, M4, and M5 mAChRs (Kis = 7.08, 44.67, 45.71, and 9.33 nM, respectively). Darifenacin selectively inhibits contractions in isolated guinea pig ileum, bladder, and trachea (pA2s = 9.44, 8.66, and 8.7, respectively), tissues that endogenously express high levels of M3 mAChRs, over isolated rabbit vas deferens and isolated guinea pig atria (pA2s = 7.9 and 7.48, respectively), which endogenously express M1 and M2 mAChRs, respectively. It inhibits micturition pressure (ED50 = 0.089 mg/kg, i.v.), as well as micturition interval and volume in rats. Formulations containing darifenacin have been used in the treatment of overactive bladder.
• Uses: Darifenacin hydrobromide is used as a medication to treat urinary incontinence. It works by blocking the M3 muscarinic acetylcholine receptor. calcium replenisher acute lymphoblastic leukemia therapeutic

Technology Process of Darifenacin hydrobromide

There total 33 articles about Darifenacin hydrobromide 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: 93.2%

2,3-dihydro-5-(2-bromoethyl)benzofuran (127264-14-6) + (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate (134002-26-9) → (S)-darifenacin hydrobromide (133099-07-7)

Guidance literature:

2,3-dihydro-5-(2-bromoethyl)benzofuran; (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate; With potassium hydroxide; triethylmethylammonium chloride; In water; toluene; at 100 ℃; for 15.25h;

With hydrogen bromide; In water; toluene; Product distribution / selectivity;

Reference yield: 85.0%

(S)-2-{1-[2-(benzofuran-5-yl)ethyl]-3-pyrrolidinyl}-2,2-diphenylacetamide (133033-99-5) → (S)-darifenacin hydrobromide (133099-07-7)

Guidance literature:

(S)-2-{1-[2-(benzofuran-5-yl)ethyl]-3-pyrrolidinyl}-2,2-diphenylacetamide; With hydrogen; acetic acid; palladium 10% on activated carbon; at 45 - 50 ℃; for 6 - 7h;

With hydrogen bromide; In water; butan-1-ol; Product distribution / selectivity;

Reference yield: 84.92%

2,3-dihydro-5-(2-bromoethyl)benzofuran (127264-14-6) + 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8,103887-32-7) → (S)-darifenacin hydrobromide (133099-07-7)

Guidance literature:

2,3-dihydro-5-(2-bromoethyl)benzofuran; 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide; With potassium hydroxide; triethylmethylammonium chloride; In water; butanone; at 75 ℃; for 6h; Heating / reflux;

With hydrogen bromide; In water; butanone;

upstream raw materials:

2,3-dihydro-5-(2-bromoethyl)benzofuran

(S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate

2-(2,3-dihydrobenzofuran-5-yl)ethylchloride

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide

Downstream raw materials:

darifenacin

Refernces

• 1、 Pramanik, Chinmoy,Bapat, Kiran,Chaudhari, Ashok,Tripathy, Narendra K.,Gurjar, Mukund K.. "A new solvent system (Cyclopentyl methyl ether-water) in process development of darifenacin HBr". . p. 1591 - 1597. Retrieved 2013/02/23.
• 2、 -. "Method for obtaining 1,3-difunctionalized pyrrolidine derivatives". Page/Page column 17. . Retrieved 2010/10/19.