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Cas Database

Name	Rivaroxaban	EINECS	685-132-2
CAS No.	366789-02-8	Density	1.46 g/cm³
PSA	116.42000	LogP	3.04080
Solubility	N/A	Melting Point	228-229°C
Formula	C₁₉H₁₈ClN₃O₅S	Boiling Point	732.609 °C at 760 mmHg
Molecular Weight	435.888	Flash Point	396.868 °C
Transport Information	N/A	Appearance	N/A
Safety		Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
Synonyms	5-Chloro-N-[[(S)-3-(4-(3-oxomorpholin-4-yl)phenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-thiophene-2-carboxamide;BAY 59-7939;Xarelto;	Article Data	105

Rivaroxaban Synthetic route

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

: 42518-98-9
5-chlorothiophene-2-carbonyl chloride

: 366789-02-8
Rivaroxaban

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 3h; Product distribution / selectivity;	100%
With triethylamine In tetrahydrofuran at 20℃; for 3h; Reagent/catalyst; Solvent; Time; Concentration; Temperature;	100%
With sodium carbonate In water; acetone; toluene at 8 - 53℃; for 0.5h;	98.7%

: 42518-98-9
5-chlorothiophene-2-carbonyl chloride

: 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one diphosphate

: 366789-02-8
Rivaroxaban

Conditions

Conditions	Yield
With sodium carbonate In water; acetone at 10 - 50℃; for 0.5h;	97.5%

: (S)-N-/3-{N-[4-(3-oxomorpholine-4-yl)phenyl]-N-(ethoxycarbonyl)amino}-2-hydroxyprop-1-yl/-5-chlorothiophene-2-carboxamide

: 366789-02-8
Rivaroxaban

Conditions

Conditions	Yield
With potassium carbonate In methanol at 20℃; for 2h;	97%

: C10H11Cl2NO4S

: 438056-69-0
4-(4-aminophenyl)morpholin-3-one

: 366789-02-8
Rivaroxaban

Conditions

Conditions	Yield
In ethanol at 36℃; for 7h; Solvent;	96.4%

: 24065-33-6
5-Chlorothiophene-2-carboxylic acid

: 898543-06-1
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

: 366789-02-8
Rivaroxaban

Conditions

Conditions	Yield
Stage #1: 5-Chlorothiophene-2-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 25℃; for 0.5h; Stage #2: 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidine-3-yl]phenyl}morpholin-3-one hydrochloride In N,N-dimethyl-formamide at 34℃; for 4h;	96.3%
With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In N,N-dimethyl-formamide at 20℃; for 2.83333h; Reagent/catalyst; Cooling with ice;	95.2%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 24h; pH=8 - 9; Large scale;	94.7%

: 42518-98-9
5-chlorothiophene-2-carbonyl chloride

: 1251952-62-1
4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one methanesulfonic acid salt

: 366789-02-8
Rivaroxaban

Conditions

Conditions	Yield
With potassium hydrogencarbonate In ethanol; water; butanone at 20 - 35℃; for 0.75h; Large scale;	96%
With triethylamine In 1-methyl-pyrrolidin-2-one; toluene at 50 - 60℃; for 0.25h;	81%

: 42518-98-9
5-chlorothiophene-2-carbonyl chloride

: 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride

: 366789-02-8
Rivaroxaban

Conditions

Conditions	Yield
Stage #1: 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride With sodium carbonate In water; acetone at 8 - 12℃; Stage #2: 5-chlorothiophene-2-carbonyl chloride In water; acetone at 50 - 53℃; for 0.5h; Temperature;	95.6%
With triethylamine In N,N-dimethyl-formamide at 30 - 40℃; for 5h;	150.1 g

: 446292-10-0
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one

: 24065-33-6
5-Chlorothiophene-2-carboxylic acid

: 366789-02-8
Rivaroxaban

Conditions

Conditions	Yield
With 4-methyl-morpholine; hydrogenchloride In water; N,N-dimethyl-formamide at 20℃; for 2.83333h;	95.2%
With ortho-iodophenylboronic acid In dichloromethane at 30℃; for 48h; Reagent/catalyst; Time; Concentration; Temperature; Solvent; Dean-Stark;	85%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h;	68.9%

: 721401-53-2
5-chloro-N-{(R)‐2‐hydroxy‐3‐[4‐(3-oxo-4-morpholinyl)phenylamino]-propyl}thiophene-2-carboxamide

: 530-62-1
1,1'-carbonyldiimidazole

: 366789-02-8
Rivaroxaban

Conditions

Conditions	Yield
With dmap In acetone at 100℃; for 6h;	95.1%
In 1-methyl-pyrrolidin-2-one; toluene at 20 - 115℃; for 1.33333h;	91.5%
In 1-methyl-pyrrolidin-2-one; toluene at 20 - 110℃; for 3.5h; Inert atmosphere;	90%

: 42518-98-9
5-chlorothiophene-2-carbonyl chloride

: 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrobromide

: 366789-02-8
Rivaroxaban

Conditions

Conditions	Yield
With sodium carbonate In water; acetone at 10 - 50℃; for 0.5h;	95%
With triethylamine In ethyl acetate at 10 - 20℃; for 1h;	10 g

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