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Name	Ivabradine hydrochloride	EINECS	638-798-3
CAS No.	148849-67-6	Density	N/A
PSA	60.47000	LogP	4.04990
Solubility	N/A	Melting Point	193-196?C
Formula	C₂₇H₃₆N₂O₅^.HCl	Boiling Point	626.9 °C at 760 mmHg
Molecular Weight	505.054	Flash Point	332.9 °C
Transport Information	N/A	Appearance	N/A
Safety	60-61	Risk Codes	50/53
Molecular Structure		Hazard Symbols	N
Synonyms	2H-3-Benzazepin-2-one,3-[3-[[(3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methyl]methylamino]propyl]-1,3,4,5-tetrahydro-7,8-dimethoxy-,monohydrochloride, (S)-;	Article Data	24

Ivabradine hydrochloride Synthetic route

: 1086026-31-4
3-{3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-(methyl)amino]propyl}-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one

: 148849-67-6
ivabradine hydrochloride

Conditions

Conditions	Yield
Stage #1: 3-{3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-(methyl)amino]propyl}-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one With palladium 10% on activated carbon; hydrogen; acetic acid at 15 - 25℃; for 23h; Stage #2: With hydrogenchloride In ethyl acetate; isopropyl alcohol at 0 - 10℃; for 1h;	93.5%
Stage #1: 3-{3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-(methyl)amino]propyl}-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one With palladium 10% on activated carbon; hydrogen; ammonium formate In methanol at 25 - 30℃; Stage #2: With hydrogenchloride In dichloromethane	78%
With hydrogenchloride; hydrogen; palladium 10% on activated carbon In water at 45℃; under 7500.75 Torr; for 6h;
Multi-step reaction with 2 steps 1: hydrogenchloride / acetonitrile / 20 - 25 °C 2: 5%-palladium/activated carbon; hydrogen / methanol / 18 h / 30 - 35 °C / 3000.3 - 3750.38 Torr / Autoclave View Scheme
Stage #1: 3-{3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-(methyl)amino]propyl}-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one With palladium 10% on activated carbon; hydrogen In methanol at 25 - 30℃; under 5250.53 - 6000.6 Torr; Stage #2: With hydrogenchloride In dichloromethane; water	24.48 g

: 3-(2-[1,3]-dioxolan-2-yl-ethyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one

: 866783-13-3
1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride

: 148849-67-6
ivabradine hydrochloride

Conditions

Conditions	Yield
Stage #1: 3-(2-[1,3]-dioxolan-2-yl-ethyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one With hydrogen; palladium on activated charcoal In ethanol at 55℃; under 3750.38 Torr; Stage #2: 1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride In ethanol; water at 20 - 85℃; under 22502.3 Torr;	85%
Stage #1: 3-(2-[1,3]-dioxolan-2-yl-ethyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one With palladium on activated charcoal; hydrogen In ethanol at 55℃; under 3750.38 Torr; Autoclave; Large scale; Stage #2: 1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride With palladium on activated charcoal; hydrogen In ethanol; water at 85℃; under 22502.3 Torr; Autoclave; Large scale;	85%
Stage #1: 3-(2-[1,3]-dioxolan-2-yl-ethyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one With palladium on activated charcoal; hydrogen In ethanol at 20 - 55℃; under 3750380 Torr; Autoclave; Inert atmosphere; Stage #2: 1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride In ethanol; water at 20 - 85℃; under 63756400 Torr; Inert atmosphere;	85%

: 3-[2-(1,3-Dioxolan-2-yl)-ethyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

: 866783-13-3
1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride

: 148849-67-6
ivabradine hydrochloride

Conditions

Conditions	Yield
With palladium on activated charcoal; hydrogen In ethanol; water at 85℃; under 22502.3 Torr; Autoclave;	85%

: 155974-00-8
ivabradine

: 148849-67-6
ivabradine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In water; acetonitrile at 20℃; pH=2;	81%
With hydrogenchloride In acetonitrile at 60℃; pH=2 - 3;	80.1%
With hydrogenchloride In diethyl ether; acetonitrile Product distribution / selectivity;	78%

: 1086026-38-1
3-[3-({[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}(methyl)amino)propyl]-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one hydrochloride

: 148849-67-6
ivabradine hydrochloride

Conditions

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In methanol at 30 - 35℃; under 3000.3 - 3750.38 Torr; for 18h; Autoclave;	80%

: 866783-13-3
1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride

: 148849-67-6
ivabradine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: potassium carbonate / water / 0.08 h 2.2: Inert atmosphere 3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme
Multi-step reaction with 2 steps 1: triethylamine / acetonitrile / 12 h / 20 °C 2: hydrogenchloride; pyrographite / acetonitrile / 0.17 h / 70 °C / pH 2 - 3 View Scheme

: 35202-54-1
3,4-dimethoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile

: 148849-67-6
ivabradine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: potassium hydroxide; water / 4 h / Reflux 1.2: 20 °C 2.1: ethyl acetate / 1.25 h / 0 °C / Reflux 3.1: hydrogenchloride / dichloromethane; water / 0.08 h 4.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 5.1: dichloromethane; water / 0 - 10 °C 6.1: borane-THF / tetrahydrofuran / 20 - 50 °C 6.2: 0.25 h / 0 - 5 °C 6.3: 2.5 h / 0 °C / Reflux 7.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 7.2: 2 h / 20 °C 8.1: potassium carbonate / water / 0.08 h 8.2: Inert atmosphere 9.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme
Multi-step reaction with 9 steps 1.1: potassium hydroxide; water / 4 h / Reflux 1.2: 20 °C 2.1: acetone / 0.5 h / Reflux; Cooling 3.1: hydrogenchloride / ethyl acetate; water / 0.08 h / pH 3 4.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 5.1: dichloromethane; water / 0 - 10 °C 6.1: borane-THF / tetrahydrofuran / 20 - 50 °C 6.2: 0.25 h / 0 - 5 °C 6.3: 2.5 h / 0 °C / Reflux 7.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 7.2: 2 h / 20 °C 8.1: potassium carbonate / water / 0.08 h 8.2: Inert atmosphere 9.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme
Multi-step reaction with 9 steps 1.1: potassium hydroxide; water / 4 h / Reflux 1.2: 20 °C 2.1: ethyl acetate / 1 h / 18 °C / Heating 3.1: hydrogenchloride / dichloromethane; water / 0.33 h 4.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 5.1: dichloromethane; water / 0 - 10 °C 6.1: borane-THF / tetrahydrofuran / 20 - 50 °C 6.2: 0.25 h / 0 - 5 °C 6.3: 2.5 h / 0 °C / Reflux 7.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 7.2: 2 h / 20 °C 8.1: potassium carbonate / water / 0.08 h 8.2: Inert atmosphere 9.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

: 148849-67-6
ivabradine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: ethyl acetate / 1.25 h / 0 °C / Reflux 2.1: hydrogenchloride / dichloromethane; water / 0.08 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C 7.1: potassium carbonate / water / 0.08 h 7.2: Inert atmosphere 8.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme
Multi-step reaction with 8 steps 1.1: acetone / 0.5 h / Reflux; Cooling 2.1: hydrogenchloride / ethyl acetate; water / 0.08 h / pH 3 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C 7.1: potassium carbonate / water / 0.08 h 7.2: Inert atmosphere 8.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme
Multi-step reaction with 8 steps 1.1: ethyl acetate / 1 h / 18 °C / Heating 2.1: hydrogenchloride / dichloromethane; water / 0.33 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C 7.1: potassium carbonate / water / 0.08 h 7.2: Inert atmosphere 8.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme
Multi-step reaction with 8 steps 1.1: ethyl acetate / 1 h / 18 °C / Heating 2.1: hydrogenchloride / dichloromethane; water / 0.33 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C 7.1: potassium carbonate / water / 0.08 h 7.2: Inert atmosphere 8.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme
Multi-step reaction with 8 steps 1.1: ethyl acetate / Heating 2.1: hydrogenchloride / dichloromethane; water / 0.33 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C 7.1: potassium carbonate / water / 0.08 h 7.2: Inert atmosphere 8.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme

: (S)-3,4-dimethoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid (+)-cinchonine

: 148849-67-6
ivabradine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: hydrogenchloride / dichloromethane; water / 0.08 h 2.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 3.1: dichloromethane; water / 0 - 10 °C 4.1: borane-THF / tetrahydrofuran / 20 - 50 °C 4.2: 0.25 h / 0 - 5 °C 4.3: 2.5 h / 0 °C / Reflux 5.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 5.2: 2 h / 20 °C 6.1: potassium carbonate / water / 0.08 h 6.2: Inert atmosphere 7.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme

Yield

Multi-step reaction with 7 steps
1.1: hydrogenchloride / dichloromethane; water / 0.08 h
2.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
3.1: dichloromethane; water / 0 - 10 °C
4.1: borane-THF / tetrahydrofuran / 20 - 50 °C
4.2: 0.25 h / 0 - 5 °C
4.3: 2.5 h / 0 °C / Reflux
5.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere
5.2: 2 h / 20 °C
6.1: potassium carbonate / water / 0.08 h
6.2: Inert atmosphere
7.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr
View Scheme

: 1220993-44-1
(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid

: 148849-67-6
ivabradine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 2.1: dichloromethane; water / 0 - 10 °C 3.1: borane-THF / tetrahydrofuran / 20 - 50 °C 3.2: 0.25 h / 0 - 5 °C 3.3: 2.5 h / 0 °C / Reflux 4.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 4.2: 2 h / 20 °C 5.1: potassium carbonate / water / 0.08 h 5.2: Inert atmosphere 6.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme
Multi-step reaction with 3 steps 1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 20 °C 1.2: 20 °C 2.1: borane-THF / tetrahydrofuran / 20 °C 2.2: 4 h 3.1: hydrogen; palladium on activated charcoal / ethanol / 55 °C / 3750.38 Torr / Autoclave; Large scale 3.2: 85 °C / 22502.3 Torr / Autoclave; Large scale View Scheme

Yield

Multi-step reaction with 6 steps
1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C
2.1: dichloromethane; water / 0 - 10 °C
3.1: borane-THF / tetrahydrofuran / 20 - 50 °C
3.2: 0.25 h / 0 - 5 °C
3.3: 2.5 h / 0 °C / Reflux
4.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere
4.2: 2 h / 20 °C
5.1: potassium carbonate / water / 0.08 h
5.2: Inert atmosphere
6.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr
View Scheme

Multi-step reaction with 3 steps
1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 20 °C
1.2: 20 °C
2.1: borane-THF / tetrahydrofuran / 20 °C
2.2: 4 h
3.1: hydrogen; palladium on activated charcoal / ethanol / 55 °C / 3750.38 Torr / Autoclave; Large scale
3.2: 85 °C / 22502.3 Torr / Autoclave; Large scale
View Scheme

Ivabradine hydrochloride Chemical Properties

Molecular Structure of Ivabradine HCl (CAS NO.148849-67-6):

IUPAC Name: 3-[3-[[(7S)-3,4-Dimethoxy-7-bicyclo[4.2.0]octa-1,3,5-trienyl]methyl-methylamino]propyl]-7,8-dimethoxy-2,5-dihydro-1H-3-benzazepin-4-one hydrochloride
Molecular Formula: C₂₇H₃₆N₂O₅^.HCl
Molecular Weight: 505.05
H-Bond Donor: 1
H-Bond Acceptor: 6
Flash Point: 332.9 °C
Enthalpy of Vaporization: 92.79 kJ/mol
Boiling Point: 626.9 °C at 760 mmHg
Vapour Pressure: 1.24E-15 mmHg at 25 °C
Product Categories: Intermediates & Fine Chemicals; Pharmaceuticals
SMILES: Cl.O=C2N(CCc1cc(OC)c(OC)cc1C2)CCCN(C[C@@H]4c3cc(OC)c(OC)cc3C4)C
InChI: InChI=1/C27H36N2O5.ClH/c1-28(17-21-11-20-14-25(33-4)26(34-5)16-22(20)21)8-6-9-29-10-7-18-12-23(31-2)24(32-3)13-19(18)15-27(29)30;/h12-14,16,21H,6-11,15,17H2,1-5H3;1H/t21-;/m1./s1
InChIKey: HLUKNZUABFFNQS-ZMBIFBSDBJ

Ivabradine hydrochloride Uses

Ivabradine HCl (CAS NO.148849-67-6) is used as selective bradycardic agent with direct effect on the pacemake, if current of the sinoatrial node.

Ivabradine hydrochloride Specification

Ivabradine HCl (CAS NO.148849-67-6), its Synonyms are (7,8-Dimethoxy 3-(3-(((1S)-(4,5-dimethoxybenzocyclobutan-1-yl)methyl)methylamino)propyl)-1,3,4,5-tetrahydro-2H-benzazepin-2-one hydrochloride ; Ivabradine hydrochloride ; 2H-3-Benzazepin-2-one, 3-(3-((((7S)-3,4-dimethoxybicyclo(4.2.0)octa-1,3,5-trien-7-yl)methyl)methylamino)propyl)-1,3,4,5-tetrahydro-7,8-dimethoxy-, monohydrochloride ; 2H-3-Benzazepin-2-one, 3-(3-(((3,4-dimethoxybicyclo(4.2.0)octa-1,3,5-trien-7-yl)methyl)methylamino)propyl)-1,3,4,5-tetrahydro-7,8-dimethoxy-, monohydrochloride, (S)- .

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