Omecamtiv mecarbil

Base Information

• Chemical Name: Omecamtiv mecarbil
• CAS No.: 873697-71-3
• Molecular Formula: C20H24FN5O3
• Molecular Weight: 401.441
• European Community (EC) Number: 850-774-6
• UNII: 2M19539ERK
• ChEMBL ID: CHEMBL1800955
• DSSTox Substance ID: DTXSID901025949
• Metabolomics Workbench ID: 152911
• NCI Thesaurus Code: C166579
• Nikkaji Number: J2.948.681F
• Wikidata: Q7089956
• Wikipedia: Omecamtiv_mecarbil
• Mol file: 873697-71-3.mol

Synonyms:AMG-423;CK 1827452;CK-1827452;omecamtiv mecarbil

Chemical Property of Omecamtiv mecarbil

Chemical Property:

• Melting Point: 180℃
• Boiling Point: 456.78 °C at 760 mmHg
• Flash Point: 230.052 °C
• PSA: 90.29000
• Density: 1.344 g/cm³
• LogP: 3.01950
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 40.25mg/L at 25℃
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 401.18631781
• Heavy Atom Count: 29
• Complexity: 558

Purity/Quality:

98% ^*data from raw suppliers

CK1827452 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC=C(C=C1)NC(=O)NC2=CC=CC(=C2F)CN3CCN(CC3)C(=O)OC
• Recent ClinicalTrials: Study to Assess the Effect of Omecamtiv Mecarbil on Exercise Capacity in Subjects With Heart Failure
• Recent EU Clinical Trials: Omecamtiv Mecarbil Post-trial Access Protocol for Subjects Completing Study 20110203 GALACTIC-HF
• Description: Omecamtiv mecarbil (CK-1827452) is a specific cardiac myosin activator and a clinical drug for left ventricular systolic heart failure. Phase 2.
• Uses: CK 1827452 is a promising new drug in systolic heart failure. It accelerates the transition of myosin into the force-generating state without affecting cardiac myocyte calcium homeostasis. CK 1827452 increases cardiac function by increasing the duration of ejection without changing the rates of contraction. CK 1827452 is a promising new drug in systolic heart failure. It accelerates the transition of myosin into the force-generating state without affecting cardiac myocyte calcium homeostasis. CK 1827452 increases cardiac function by increasing the duration of ejection without changing the rates of contraction.

Technology Process of Omecamtiv mecarbil

There total 30 articles about Omecamtiv mecarbil 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: 86.0%

5-isocyanato-2-methylpyridine (732245-99-7) + methyl 4-(3-amino-2-fluorobenzyl)piperazine-1-carboxylate (873697-70-2) → methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate (873697-71-3)

Guidance literature:

In acetone; at 20 ℃; Heating/reflux;

Reference yield: 82.0%

methyl 4-(3-amino-2-fluorobenzyl)piperazine-1-carboxylate (873697-70-2) + phenyl (6-methylpyridin-3-yl)carbamate hydrochloride (1628206-34-7) → methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate (873697-71-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; acetonitrile; at 57 ℃; for 21h; Industrial scale;

DOI:10.1021/acs.oprd.9b00200

Reference yield: 81.0%

5-Amino-2-methylpyridine (80287-53-2,3430-14-6) + C20H22FN3O4 → methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate (873697-71-3)

Guidance literature:

In toluene; at 80 ℃; for 15h; Inert atmosphere;

DOI:10.1021/ja305212v

upstream raw materials:

methyl piperazine-1,3-carboxylate hydrochloride

5-isocyanato-2-methylpyridine

tert-butyl 4-(3-amino-2-fluorobenzyl)piperazine-1-carboxylate

methyl 4-(3-amino-2-fluorobenzyl)piperazine-1-carboxylate

Refernces

• 1、 -. "SYNTHESIS OF OMECAMTIV MECARBIL". . . Retrieved 2019/01/17.
• 2、 Vinogradova, Ekaterina V.,Fors, Brett P.,Buchwald, Stephen L.. "Palladium-catalyzed cross-coupling of aryl chlorides and triflates with sodium cyanate: A practical synthesis of unsymmetrical ureas". supporting information; experimental part. p. 11132 - 11135. Retrieved 2012/08/28.