Omecamtiv mecarbil supplier | CasNO.873697-71-3

Name
Omecamtiv mecarbil
EINECS
CAS No. 873697-71-3
Article Data11
CAS DataBase
Density 1.344 g/cm³
Solubility 40.25mg/L at 25℃
Melting Point 180℃
Formula C₂₀H₂₄FN₅O₃
Boiling Point 456.78 °C at 760 mmHg
Molecular Weight 401.441
Flash Point 230.052 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms CK 1827452;UNII-2M19539ERK;Methyl 4-((2-fluoro-3-(((6-methylpyridin-3-yl)carbamoyl)amino)phenyl)methyl) piperazine-1-carboxylate;
PSA 90.29000
LogP 3.01950

Synthetic route

: 732245-99-7
5-isocyanato-2-methylpyridine

: 873697-70-2
methyl 4-(3-amino-2-fluorobenzyl)piperazine-1-carboxylate

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
In acetone at 20℃; Heating/reflux;	86%
In acetone at 20℃; Heating / reflux;	86%
In acetone at 20℃; for 6.65h; Heating / reflux;	86%
In acetone at 20℃; Heating / reflux;	73%
In acetone for 6.5h; Heating / reflux;	73%

: 873697-70-2
methyl 4-(3-amino-2-fluorobenzyl)piperazine-1-carboxylate

: 1628206-34-7
phenyl (6-methylpyridin-3-yl)carbamate hydrochloride

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; acetonitrile at 57℃; for 21h; Industrial scale;	82%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 55℃; for 18h;	47 g

: 80287-53-2, 3430-14-6
5-Amino-2-methylpyridine

: C20H22FN3O4

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
In toluene at 80℃; for 15h; Inert atmosphere;	81%

: 873697-70-2
methyl 4-(3-amino-2-fluorobenzyl)piperazine-1-carboxylate

: C13H12N2O2*(x)ClH

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; acetonitrile	80%

: 732245-99-7
5-isocyanato-2-methylpyridine

: 942224-53-5
tert-butyl 4-(3-amino-2-fluorobenzyl)piperazine-1-carboxylate

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
In acetone at 20℃; for 5.65h; Heating / reflux;	73%

: 3430-13-5
5-bromo-2-methylpyridine

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: t-BuBrettPhos; palladium diacetate; caesium carbonate / tetrahydrofuran; water / 2 h / 85 °C / Inert atmosphere 2: hydrogenchloride; palladium on carbon; hydrogen / methanol; water / 20 h / 20 °C / 760.05 Torr 3: t-BuBrettPhos; palladium diacetate; caesium carbonate / tetrahydrofuran; water / Inert atmosphere; Heating View Scheme

: 1-(bromomethyl)-3-chloro-2-fluorobenzene

: 50606-31-0
methyl piperazine-1-carboxylate

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1.25 h / 20 °C / Inert atmosphere 2: t-BuBrettPhos; palladium diacetate; caesium carbonate / tetrahydrofuran; water / Inert atmosphere; Heating View Scheme

: C14H15N3O

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride; palladium on carbon; hydrogen / methanol; water / 20 h / 20 °C / 760.05 Torr 2: t-BuBrettPhos; palladium diacetate; caesium carbonate / tetrahydrofuran; water / Inert atmosphere; Heating View Scheme

: 1309439-44-8
(2-methylpyridin-5-yl)urea

: 1309439-45-9
methyl 4-(3-chloro-2-fluorobenzyl)piperazine-1-carboxylate

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
With t-BuBrettPhos; palladium diacetate; caesium carbonate In tetrahydrofuran; water Inert atmosphere; Heating;	253 mg

: 1-(bromomethyl)-3-chloro-2-fluorobenzene

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 6 h / 20 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos; triethylamine / toluene / 16 h / 120 °C / Inert atmosphere 3: toluene / 15 h / 80 °C / Inert atmosphere View Scheme

: 50606-31-0
methyl piperazine-1-carboxylate

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 6 h / 20 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos; triethylamine / toluene / 16 h / 120 °C / Inert atmosphere 3: toluene / 15 h / 80 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: phosphoric acid / water; tert-butyl methyl ether / 6 h / 20 - 40 °C / Industrial scale 2: N-ethyl-N,N-diisopropylamine; sodium hydroxide / toluene; methanol / 7.5 h / 25 - 40 °C / Inert atmosphere; Industrial scale 3: hydrogen; 0.7% Pd/C / 5 h / 15 °C / 3102.97 Torr 4: N-ethyl-N,N-diisopropylamine / acetonitrile; tetrahydrofuran / 21 h / 57 °C / Industrial scale View Scheme
Multi-step reaction with 4 steps 1: phosphoric acid / water; tert-butyl methyl ether / 6 h / 20 - 40 °C / Industrial scale 2: N-ethyl-N,N-diisopropylamine; sodium hydroxide / toluene; methanol / 7.5 h / 25 - 40 °C / Inert atmosphere; Industrial scale 3: hydrogen; 5%-palladium/activated carbon / water; toluene; ethanol / 10 - 15 °C / 3102.97 Torr / Industrial scale 4: N-ethyl-N,N-diisopropylamine / acetonitrile; tetrahydrofuran / 21 h / 57 °C / Industrial scale View Scheme

: 1309439-45-9
methyl 4-(3-chloro-2-fluorobenzyl)piperazine-1-carboxylate

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos; triethylamine / toluene / 16 h / 120 °C / Inert atmosphere 2: toluene / 15 h / 80 °C / Inert atmosphere View Scheme

: 80287-53-2, 3430-14-6
5-Amino-2-methylpyridine

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetonitrile / 7 h / 20 °C 2: N-ethyl-N,N-diisopropylamine / acetonitrile; tetrahydrofuran View Scheme

: 21203-68-9
2-methyl-5-nitropyridine

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen; 5%-palladium/activated carbon / 50 - 60 °C / 3375.34 Torr 2: acetonitrile / 7 h / 20 °C 3: N-ethyl-N,N-diisopropylamine / acetonitrile; tetrahydrofuran View Scheme

: 437-86-5
2-fluoro-3-nitrotoluene

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide; dibenzoyl peroxide; acetic acid / 8 h / 83 °C 1.2: 3 h / 40 °C 2.1: sodium hydroxide / water; toluene / 1 h / 20 °C 2.2: 15 °C / 3000.3 Torr 3.1: N-ethyl-N,N-diisopropylamine / acetonitrile; tetrahydrofuran View Scheme
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; dibenzoyl peroxide; acetic acid; sodium hydroxide / water / 18.5 h / 83 °C / Inert atmosphere; Industrial scale 1.2: 7.5 h / 40 °C / Industrial scale 2.1: N-ethyl-N,N-diisopropylamine; sodium hydroxide / toluene; methanol / 7.5 h / 25 - 40 °C / Inert atmosphere; Industrial scale 3.1: hydrogen; 0.7% Pd/C / 5 h / 15 °C / 3102.97 Torr 4.1: N-ethyl-N,N-diisopropylamine / acetonitrile; tetrahydrofuran / 21 h / 57 °C / Industrial scale View Scheme
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; dibenzoyl peroxide; acetic acid; sodium hydroxide / water / 18.5 h / 83 °C / Inert atmosphere; Industrial scale 1.2: 7.5 h / 40 °C / Industrial scale 2.1: N-ethyl-N,N-diisopropylamine; sodium hydroxide / toluene; methanol / 7.5 h / 25 - 40 °C / Inert atmosphere; Industrial scale 3.1: hydrogen; 5%-palladium/activated carbon / water; toluene; ethanol / 10 - 15 °C / 3102.97 Torr / Industrial scale 4.1: N-ethyl-N,N-diisopropylamine / acetonitrile; tetrahydrofuran / 21 h / 57 °C / Industrial scale View Scheme
Multi-step reaction with 4 steps 1: N-Bromosuccinimide; dibenzoyl peroxide; acetic acid; sodium hydroxide / water / 18.5 h / 83 °C / Inert atmosphere; Industrial scale 2: N-ethyl-N,N-diisopropylamine; sodium hydroxide / toluene; methanol / 7.5 h / 25 - 40 °C / Inert atmosphere; Industrial scale 3: hydrogen; 0.7% Pd/C / 5 h / 15 °C / 3102.97 Torr 4: N-ethyl-N,N-diisopropylamine / acetonitrile; tetrahydrofuran / 21 h / 57 °C / Industrial scale View Scheme
Multi-step reaction with 4 steps 1: N-Bromosuccinimide; dibenzoyl peroxide; acetic acid; sodium hydroxide / water / 18.5 h / 83 °C / Inert atmosphere; Industrial scale 2: N-ethyl-N,N-diisopropylamine; sodium hydroxide / toluene; methanol / 7.5 h / 25 - 40 °C / Inert atmosphere; Industrial scale 3: hydrogen; 5%-palladium/activated carbon / water; toluene; ethanol / 10 - 15 °C / 3102.97 Torr / Industrial scale 4: N-ethyl-N,N-diisopropylamine / acetonitrile; tetrahydrofuran / 21 h / 57 °C / Industrial scale View Scheme

: methyl 4-(2-fluoro-3-nitrobenzyl)piperazine-1-carboxylate hydrochloride

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water; toluene / 1 h / 20 °C 1.2: 15 °C / 3000.3 Torr 2.1: N-ethyl-N,N-diisopropylamine / acetonitrile; tetrahydrofuran View Scheme

: piperazine methyl carboxylate hemiphosphate hemihydrate

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide; dibenzoyl peroxide; acetic acid / 8 h / 83 °C 1.2: 3 h / 40 °C 2.1: sodium hydroxide / water; toluene / 1 h / 20 °C 2.2: 15 °C / 3000.3 Torr 3.1: N-ethyl-N,N-diisopropylamine / acetonitrile; tetrahydrofuran View Scheme

: methyl 4-(2-fluoro-3-nitrobenzyl)piperazine-1-carboxylate

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen; 5%-palladium/activated carbon / water; toluene; ethanol / 10 - 15 °C / 3102.97 Torr / Industrial scale 2: N-ethyl-N,N-diisopropylamine / acetonitrile; tetrahydrofuran / 21 h / 57 °C / Industrial scale View Scheme
Multi-step reaction with 2 steps 1: hydrogen; 0.7% Pd/C / 5 h / 15 °C / 3102.97 Torr 2: N-ethyl-N,N-diisopropylamine / acetonitrile; tetrahydrofuran / 21 h / 57 °C / Industrial scale View Scheme

: methyl 4-(2-fluoro-3-nitrobenzyl)piperazine-1-carboxylate hydrochloride

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / water; toluene / 0.25 h / Industrial scale 2: hydrogen; 0.7% Pd/C / 5 h / 15 °C / 3102.97 Torr 3: N-ethyl-N,N-diisopropylamine / acetonitrile; tetrahydrofuran / 21 h / 57 °C / Industrial scale View Scheme
Multi-step reaction with 3 steps 1: sodium hydroxide / water; toluene / 0.25 h / Industrial scale 2: hydrogen; 5%-palladium/activated carbon / water; toluene; ethanol / 10 - 15 °C / 3102.97 Torr / Industrial scale 3: N-ethyl-N,N-diisopropylamine / acetonitrile; tetrahydrofuran / 21 h / 57 °C / Industrial scale View Scheme

: C6H12N2O2*0.67H3O4P

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; sodium hydroxide / toluene; methanol / 7.5 h / 25 - 40 °C / Inert atmosphere; Industrial scale 2: hydrogen; 5%-palladium/activated carbon / water; toluene; ethanol / 10 - 15 °C / 3102.97 Torr / Industrial scale 3: N-ethyl-N,N-diisopropylamine / acetonitrile; tetrahydrofuran / 21 h / 57 °C / Industrial scale View Scheme
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; sodium hydroxide / toluene; methanol / 7.5 h / 25 - 40 °C / Inert atmosphere; Industrial scale 2: hydrogen; 0.7% Pd/C / 5 h / 15 °C / 3102.97 Torr 3: N-ethyl-N,N-diisopropylamine / acetonitrile; tetrahydrofuran / 21 h / 57 °C / Industrial scale View Scheme

: 946125-65-1
1-(bromomethyl)-2-fluoro-3- nitrobenzene

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; sodium hydroxide / toluene; methanol / 7.5 h / 25 - 40 °C / Inert atmosphere; Industrial scale 2: hydrogen; 5%-palladium/activated carbon / water; toluene; ethanol / 10 - 15 °C / 3102.97 Torr / Industrial scale 3: N-ethyl-N,N-diisopropylamine / acetonitrile; tetrahydrofuran / 21 h / 57 °C / Industrial scale View Scheme
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; sodium hydroxide / toluene; methanol / 7.5 h / 25 - 40 °C / Inert atmosphere; Industrial scale 2: hydrogen; 0.7% Pd/C / 5 h / 15 °C / 3102.97 Torr 3: N-ethyl-N,N-diisopropylamine / acetonitrile; tetrahydrofuran / 21 h / 57 °C / Industrial scale View Scheme

: 1195768-18-3
methyl 3-amino-2-fluoro-benzoate

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22.25 h / 0 - 65 °C 2.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 2.5 h / 65 °C 3.1: methanesulfonyl chloride; triethylamine / dichloromethane / 3.25 h / 0 - 28 °C 3.2: 16 h / 0 - 28 °C View Scheme
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 1 h / 5 - 28 °C 1.2: 2 h / 28 °C 2.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 2.5 h / 65 °C 3.1: methanesulfonyl chloride; triethylamine / dichloromethane / 3.25 h / 0 - 28 °C 3.2: 16 h / 0 - 28 °C View Scheme

: methyl 2-fluoro-3-(3-(6-methylpyridin-3-yl)ureido)benzoate

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 2.5 h / 65 °C 2.1: methanesulfonyl chloride; triethylamine / dichloromethane / 3.25 h / 0 - 28 °C 2.2: 16 h / 0 - 28 °C View Scheme

: 50606-31-0
methyl piperazine-1-carboxylate

: 1-(2-fluoro-3-(hydroxymethyl)phenyl)-3-(6-methylpyridin-3-yl)urea

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: 1-(2-fluoro-3-(hydroxymethyl)phenyl)-3-(6-methylpyridin-3-yl)urea With methanesulfonyl chloride; triethylamine In dichloromethane at 0 - 28℃; for 3.25h; Stage #2: methyl piperazine-1-carboxylate With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 0 - 28℃; for 16h;

: 873697-75-7
methyl piperazine-1,3-carboxylate hydrochloride

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium hydroxide / dichloromethane / 1 h / 30 °C 2.1: methanesulfonyl chloride; triethylamine / dichloromethane / 3.25 h / 0 - 28 °C 2.2: 16 h / 0 - 28 °C View Scheme

: 1-(3-cyano-2-fluorophenyl)-3-(6-methylpyridin-3-yl)urea

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: water; sodium hydroxide / ethanol / 24.42 h / 30 - 100 °C 2.1: thionyl chloride; methanol / 16.17 h / 0 - 65 °C 3.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 2.5 h / 65 °C 4.1: methanesulfonyl chloride; triethylamine / dichloromethane / 3.25 h / 0 - 28 °C 4.2: 16 h / 0 - 28 °C View Scheme

: 2-fluoro-3-(3-(6-methylpyridin-3-yl)ureido)benzoic acid

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: thionyl chloride; methanol / 16.17 h / 0 - 65 °C 2.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 2.5 h / 65 °C 3.1: methanesulfonyl chloride; triethylamine / dichloromethane / 3.25 h / 0 - 28 °C 3.2: 16 h / 0 - 28 °C View Scheme

: 80287-53-2, 3430-14-6
5-Amino-2-methylpyridine

: 873697-70-2
methyl 4-(3-amino-2-fluorobenzyl)piperazine-1-carboxylate

: 32315-10-9
bis(trichloromethyl) carbonate

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: methyl 4-(3-amino-2-fluorobenzyl)piperazine-1-carboxylate; bis(trichloromethyl) carbonate With triethylamine In dichloromethane at 5 - 28℃; for 1h; Stage #2: 5-Amino-2-methylpyridine In dichloromethane at 28℃; for 2h;

...Expand

: 873697-68-8
3-amino-2-fluorobenzonitrile

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 0 - 65 °C 2.1: water; sodium hydroxide / ethanol / 24.42 h / 30 - 100 °C 3.1: thionyl chloride; methanol / 16.17 h / 0 - 65 °C 4.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 2.5 h / 65 °C 5.1: methanesulfonyl chloride; triethylamine / dichloromethane / 3.25 h / 0 - 28 °C 5.2: 16 h / 0 - 28 °C View Scheme
Multi-step reaction with 5 steps 1.1: water; sodium hydroxide / 14 h / 30 - 100 °C 2.1: thionyl chloride / 16.5 h / 0 - 65 °C 3.1: triethylamine / dichloromethane / 1 h / 5 - 28 °C 3.2: 2 h / 28 °C 4.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 2.5 h / 65 °C 5.1: methanesulfonyl chloride; triethylamine / dichloromethane / 3.25 h / 0 - 28 °C 5.2: 16 h / 0 - 28 °C View Scheme
Multi-step reaction with 5 steps 1.1: water; sodium hydroxide / 14 h / 30 - 100 °C 2.1: thionyl chloride / 16.5 h / 0 - 65 °C 3.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22.25 h / 0 - 65 °C 4.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 2.5 h / 65 °C 5.1: methanesulfonyl chloride; triethylamine / dichloromethane / 3.25 h / 0 - 28 °C 5.2: 16 h / 0 - 28 °C View Scheme

: 914223-43-1
3-amino-2-fluoro benzoic acid

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: thionyl chloride / 16.5 h / 0 - 65 °C 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22.25 h / 0 - 65 °C 3.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 2.5 h / 65 °C 4.1: methanesulfonyl chloride; triethylamine / dichloromethane / 3.25 h / 0 - 28 °C 4.2: 16 h / 0 - 28 °C View Scheme
Multi-step reaction with 4 steps 1.1: thionyl chloride / 16.5 h / 0 - 65 °C 2.1: triethylamine / dichloromethane / 1 h / 5 - 28 °C 2.2: 2 h / 28 °C 3.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 2.5 h / 65 °C 4.1: methanesulfonyl chloride; triethylamine / dichloromethane / 3.25 h / 0 - 28 °C 4.2: 16 h / 0 - 28 °C View Scheme

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

: C20H24FN5O3*2H2O4S

Conditions

Conditions	Yield
With hydrogenchloride; sulfuric acid In tetrahydrofuran; methanol at 50℃; for 4h;

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

: C20H24FN5O3*(x)H2O4S

Conditions

Conditions	Yield
With sulfuric acid In acetone

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

: 594-45-6
ethanesulfonic acid

: (x)C2H6O3S*C20H24FN5O3

Conditions

Conditions	Yield
In tetrahydrofuran; acetone

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

: 110-17-8
(2E)-but-2-enedioic acid

: omecamtiv mecarbil fumaric acid salt

Conditions

Conditions	Yield
With hydrogenchloride In methanol; hexane; water; acetone; acetonitrile at 50℃; for 4h;
In tetrahydrofuran at 65℃;

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

: 110-16-7
maleic acid

: omecamtiv mecarbil maleic acid salt

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water; acetone at 50℃; for 4h; Temperature;
In methanol at 65℃; Solvent; Temperature;

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

: 141-82-2
malonic acid

: C20H24FN5O3*2C3H4O4

Conditions

Conditions	Yield
In methanol at 50℃;

: 873697-71-3
methyl 4-[(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}phenyl)methyl]piperazine-1-carboxylate

: 75-75-2
methanesulfonic acid

: (x)CH4O3S*C20H24FN5O3

Conditions

Conditions	Yield
In methanol at 50℃;

Omecamtiv mecarbil Specification

The Omecamtiv mecarbil, also known as CK 1827452, is an organic compound with the formula C₂₀H₂₄FN₅O₃. With the CAS registry number 873697-71-3, its systematic name is methyl 4-(2-fluoro-3-{[(6-methylpyridin-3-yl)carbamoyl]amino}benzyl)piperazine-1-carboxylate. This chemical's classification code is Treatment of Heart Failure; a Cardiac Inotrope. What's more, it is a cardiac specific myosin activator. It is clinically tested for its role in the treatment of left ventricular systolic heart failure.

Physical properties of Omecamtiv mecarbil: (1)ACD/LogP: 1.40; (2)#H bond acceptors: 8; (3)#H bond donors: 2; (4)#Freely Rotating Bonds: 5; (5)Index of Refraction: 1.639; (6)Molar Refractivity: 107.427 cm³; (7)Molar Volume: 298.625 cm³; (8)Surface Tension: 64.952 dyne/cm; (9)Density: 1.344 g/cm³; (10)Flash Point: 230.052 °C; (11)Enthalpy of Vaporization: 71.679 kJ/mol; (12)Boiling Point: 456.78 °C at 760 mmHg; (13)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(Nc1ccc(nc1)C)Nc2c(F)c(ccc2)CN3CCN(C(=O)OC)CC3
(2)InChI: InChI=1/C20H24FN5O3/c1-14-6-7-16(12-22-14)23-19(27)24-17-5-3-4-15(18(17)21)13-25-8-10-26(11-9-25)20(28)29-2/h3-7,12H,8-11,13H2,1-2H3,(H2,23,24,27)
(3)InChIKey: RFUBTTPMWSKEIW-UHFFFAOYAF

Product Name

Omecamtiv mecarbil

Synthetic route

Omecamtiv mecarbil Specification

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