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Basic Information
| CAS No.: | 366789-02-8 |
|---|---|
| Name: | Rivaroxaban |
| Article Data: | 105 |
| Molecular Structure: | |
|
|
|
| Formula: | C19H18ClN3O5S |
| Molecular Weight: | 435.888 |
| 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; |
| EINECS: | 685-132-2 |
| Density: | 1.46 g/cm3 |
| Melting Point: | 228-229°C |
| Boiling Point: | 732.609 °C at 760 mmHg |
| Flash Point: | 396.868 °C |
| PSA: | 116.42000 |
| LogP: | 3.04080 |
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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
- 366789-02-8
Rivaroxaban
Conditions
| Conditions | Yield |
|---|---|
| With sodium carbonate In water; acetone at 10 - 50℃; for 0.5h; | 97.5% |
- 366789-02-8
Rivaroxaban
Conditions
| Conditions | Yield |
|---|---|
| With potassium carbonate In methanol at 20℃; for 2h; | 97% |
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
- 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
- 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 |
Raw Materials
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