Product Name

  • Name

    Rivaroxaban

  • EINECS 685-132-2
  • CAS No. 366789-02-8
  • Article Data105
  • CAS DataBase
  • Density 1.46 g/cm3
  • Solubility
  • 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
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 366789-02-8 (Rivaroxaban)
  • Hazard Symbols
  • 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;
  • PSA 116.42000
  • LogP 3.04080

Synthetic route

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

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

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

5-chlorothiophene-2-carbonyl chloride

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
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%
5-chlorothiophene-2-carbonyl chloride
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

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

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
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

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

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
With potassium carbonate In methanol at 20℃; for 2h;97%
C10H11Cl2NO4S

C10H11Cl2NO4S

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

4-(4-aminophenyl)morpholin-3-one

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
In ethanol at 36℃; for 7h; Solvent;96.4%
5-Chlorothiophene-2-carboxylic acid
24065-33-6

5-Chlorothiophene-2-carboxylic acid

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

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

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
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%
5-chlorothiophene-2-carbonyl chloride
42518-98-9

5-chlorothiophene-2-carbonyl chloride

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

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

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
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%
5-chlorothiophene-2-carbonyl chloride
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

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

Rivaroxaban
366789-02-8

Rivaroxaban

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

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

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

5-Chlorothiophene-2-carboxylic acid

Rivaroxaban
366789-02-8

Rivaroxaban

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

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

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
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%
5-chlorothiophene-2-carbonyl chloride
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

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

Rivaroxaban
366789-02-8

Rivaroxaban

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

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

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
With potassium carbonate In water; acetonitrile at 5 - 40℃; Solvent; Temperature;95%
5-Chlorothiophene-2-carboxylic acid
24065-33-6

5-Chlorothiophene-2-carboxylic acid

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

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

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
Stage #1: 5-Chlorothiophene-2-carboxylic acid; 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate at 10 - 25℃; for 12.5h;
Stage #2: With water In ethyl acetate for 1h;		94%
5-chlorothiophene-2-carbonyl chloride
42518-98-9

5-chlorothiophene-2-carbonyl chloride

(S)-4-(4-(5-(aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one hydrobromide

(S)-4-(4-(5-(aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one hydrobromide

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
Stage #1: (S)-4-(4-(5-(aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one hydrobromide With sodium carbonate In dichloromethane at 20℃; for 1h;
Stage #2: 5-chlorothiophene-2-carbonyl chloride In dichloromethane at 0 - 20℃; for 5h; Reagent/catalyst;		93.4%
5-chlorothiophene-2-carboxylic acid chloride
89166-94-9

5-chlorothiophene-2-carboxylic acid chloride

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

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

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
With triethylamine In water; acetone; toluene at 30 - 35℃; for 2h; Temperature; Concentration;93.3%
5-chlorothiophene-2-carbonyl chloride
42518-98-9

5-chlorothiophene-2-carbonyl chloride

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

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

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
With sodium carbonate In water; acetone; toluene at 8 - 53℃;93.12%
With sodium carbonate In water; acetone; toluene at 10 - 53℃; for 0.5h; High pressure;90%
With potassium carbonate In dichloromethane at 25 - 30℃; for 5h;88%
C17H18ClN3O4S

C17H18ClN3O4S

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
With dmap In N,N-dimethyl-formamide for 6h; Reflux;93.1%
2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione
446292-08-6

2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione

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

5-Chlorothiophene-2-carboxylic acid

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
Stage #1: 2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione With methylamine In ethanol; water at 60℃; for 3h;
Stage #2: 5-Chlorothiophene-2-carboxylic acid With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In ethanol; water at 25℃; for 12h; Solvent; Temperature;		92.8%
4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one
446292-10-0

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

C11H6ClN3O2S

C11H6ClN3O2S

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
With triethylamine at 10 - 25℃;90.3%
5-chlorothiophene-2-carbonyl chloride
42518-98-9

5-chlorothiophene-2-carbonyl chloride

(5S)-4-{4-[5-(aminomethyl)-2-oxo-1,3-oxazolidine-3-yl]phenyl}morpholine-3-one nitrate

(5S)-4-{4-[5-(aminomethyl)-2-oxo-1,3-oxazolidine-3-yl]phenyl}morpholine-3-one nitrate

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
With triethylamine In dichloromethane at 10 - 20℃; for 1h; Large scale;90%
N-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide

N-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
With trichloroisocyanuric acid In acetic acid at 20 - 40℃; for 2h;90%
5-chlorothiophene-2-carbonyl chloride
42518-98-9

5-chlorothiophene-2-carbonyl chloride

4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidine-3-yl]phenyl}morpholin-3-one oxalate
1430407-73-0

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

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
With sodium carbonate In water; acetone; toluene at 50 - 55℃; for 1h; Temperature; Time;89.9%
5-Chlorothiophene-2-carboxylic acid
24065-33-6

5-Chlorothiophene-2-carboxylic acid

4-{4-[(5S)-aminomethyI-2-oxo-1,3-oxazolidine-3-yl]-phenyl}-morphoIine-3-one acetate
1411775-01-3

4-{4-[(5S)-aminomethyI-2-oxo-1,3-oxazolidine-3-yl]-phenyl}-morphoIine-3-one acetate

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
With potassium carbonate; 1,1'-carbonyldiimidazole In water; acetonitrile at 50 - 55℃; Product distribution / selectivity;89%
toluene-4-sulfonic acid (S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-2-[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyloxy]-propyl ester

toluene-4-sulfonic acid (S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-2-[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyloxy]-propyl ester

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
With lithium tert-butoxide In tetrahydrofuran at 0℃; for 1h;88.5%
toluene-4-sulfonic acid (S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-2-[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyloxy]-propyl ester
1325210-63-6

toluene-4-sulfonic acid (S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-2-[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyloxy]-propyl ester

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
With lithium tert-butoxide In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;88.5%
5-chlorothiophene-2-carbonyl chloride
42518-98-9

5-chlorothiophene-2-carbonyl chloride

4-{4-[(5S)-aminomethyI-2-oxo-1,3-oxazolidine-3-yl]-phenyl}-morphoIine-3-one acetate
1411775-01-3

4-{4-[(5S)-aminomethyI-2-oxo-1,3-oxazolidine-3-yl]-phenyl}-morphoIine-3-one acetate

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
With sodium carbonate; acetone In water; toluene at 8 - 55℃; Product distribution / selectivity;88%
5-chloro-thiophene-2-carboxylic acid-1-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-{methoxycarbonyl-[4-(3-oxo-morpholin-4-yl)-phenyl]-amino}-ethyl ester
1263103-47-4

5-chloro-thiophene-2-carboxylic acid-1-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-{methoxycarbonyl-[4-(3-oxo-morpholin-4-yl)-phenyl]-amino}-ethyl ester

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
With potassium carbonate; methylamine In water; isopropyl alcohol at 60℃; for 15h; Product distribution / selectivity;86%
5-chlorothiophene-2-carbonyl chloride
42518-98-9

5-chlorothiophene-2-carbonyl chloride

4-{4-[5-aminomethyI-2-oxo-1,3-oxazolidine-3-yl]-phenyl}-morphoIine-3-one acetate
1411711-66-4

4-{4-[5-aminomethyI-2-oxo-1,3-oxazolidine-3-yl]-phenyl}-morphoIine-3-one acetate

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
With sodium carbonate; acetone In water; toluene at 8 - 53℃;86%
5-chlorothiophene-2-carbonyl chloride
42518-98-9

5-chlorothiophene-2-carbonyl chloride

4-{4-[(S)-5-[(((4-chlorophenyl)methylene)amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-one
1414932-72-1

4-{4-[(S)-5-[(((4-chlorophenyl)methylene)amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-one

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
Stage #1: 4-{4-[(S)-5-[(((4-chlorophenyl)methylene)amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-one With hydrogenchloride In water; ethyl acetate at 20℃; for 2h;
Stage #2: 5-chlorothiophene-2-carbonyl chloride With sodium hydroxide In dichloromethane; water at 20℃; for 4h; pH=7 - 8;		83%
Stage #1: 4-{4-[(S)-5-[(((4-chlorophenyl)methylene)amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-one With hydrogenchloride In water; ethyl acetate at 20℃; for 2h;
Stage #2: 5-chlorothiophene-2-carbonyl chloride With sodium hydroxide In dichloromethane at 20℃; for 4h; pH=7 - 8;		83%
Stage #1: 4-{4-[(S)-5-[(((4-chlorophenyl)methylene)amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-one With hydrogenchloride; water In dichloromethane for 1.5h;
Stage #2: With sodium hydroxide In dichloromethane; water pH=9 - 10; Cooling with ice;
Stage #3: 5-chlorothiophene-2-carbonyl chloride In dichloromethane; water at 20℃; for 0.5h; Time; pH-value; Cooling with ice;		36.0 g
4-{4-[(5S)-5-(amino methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride
898543-06-1

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

4-nitrophenyl 5-chlorothiophene-2-carboxylate
1450877-56-1

4-nitrophenyl 5-chlorothiophene-2-carboxylate

Rivaroxaban
366789-02-8

Rivaroxaban

Conditions
ConditionsYield
With triethylamine In dimethyl sulfoxide at 35 - 40℃; Reagent/catalyst; Solvent; Temperature;82.7%
With triethylamine In dimethyl sulfoxide; acetonitrile at 35 - 40℃;82.7%
Rivaroxaban
366789-02-8

Rivaroxaban

acetic acid
64-19-7

acetic acid

rivaroxaban acetic acid

rivaroxaban acetic acid

Conditions
ConditionsYield
at 60℃; for 2h; Temperature;98%
Rivaroxaban
366789-02-8

Rivaroxaban

2-[2-({4-[(5S)-5-{[(5-chlorothiophen-2-yl)formamido]methyl}-2-oxo-1,3-oxazolidin-3-yl]phenyl}amino)ethoxy]acetic acid
931204-39-6

2-[2-({4-[(5S)-5-{[(5-chlorothiophen-2-yl)formamido]methyl}-2-oxo-1,3-oxazolidin-3-yl]phenyl}amino)ethoxy]acetic acid

Conditions
ConditionsYield
With hydrogenchloride; acetic acid In water at 60℃; for 5h;92.2%

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