| Identification | Back Directory | [Name]
1H-ISOINDOLE-1,3(2H)-DIONE, 2-[[(5S)-2-OXO-3-[4-(3-OXO-4-MORPHOLINYL)PHENYL]-5-OXAZOLIDINYL]METHYL]- | [CAS]
446292-08-6 | [Synonyms]
Rivaroxaban-5
Rivaroxaban G
Rivaroxaban ImpVI
Rivaroxaban Intermediate5
Rivaroxaban EP Impurity G
RivaroxabanInterMediates-01
Rivaroxaban Phthalimido Impurity
2-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}
2-[[(5S)-2-OXO-3-[4-(3-OXO-4-MORPHOLINYL)PHENYL]-5-OXAZOLIDINYL]METHYL]-
4-[4-[(5S)-5-PhthaliMidoMethyl-2-oxo-3-oxazolidinyl]phenyl]-3-Morpholinone
(S)-2-((2-oxo-3-(4-(3-oxoMorpholino)phenyl)oxazolidin-5-yl)Methyl)isoindoline-1,3-dione
(R)-2-((2-oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione
2-[[(5S)-2-Oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-1H-isoindole-1,3(2H)-dione
1H-ISOINDOLE-1,3(2H)-DIONE, 2-[[(5S)-2-OXO-3-[4-(3-OXO-4-MORPHOLINYL)PHENYL]-5-OXAZOLIDINYL]METHYL]-
(S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione
(Rivaroxaban)
2-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dion
2-({(5S)-2-oxo-3-[4-(3-oxoMorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}Methyl)-1H-isoindole-1,3(2H)-dione
2-[[(5S)-2-OXO-3-[4-(3-OXO-4-MORPHOLINYL)PHENYL]-5-OXAZOLIDINYL]METHYL]-1H-ISOINDOLE-1,3(2H)-DIONE CAS: 446292-08-6
2 - [[(5S) -2- oxo-3- [4- (3-oxo - (morpholin-4-yl)) phenyl] -5-oxazolidinyl] methyl] lH- isoindole -1,3 (2H) - dione
Rivaroxaban impurity 4/2-[[(5S)-2-Oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-1H-isoindole-1,3(2H)-dione | [EINECS(EC#)]
610-201-0 | [Molecular Formula]
C22H19N3O6 | [MDL Number]
MFCD11977665 | [MOL File]
446292-08-6.mol | [Molecular Weight]
421.4 |
| Chemical Properties | Back Directory | [Melting point ]
213-215°C | [Boiling point ]
702.9±55.0 °C(Predicted) | [density ]
1.465±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
0.99±0.20(Predicted) | [color ]
White to Off-White | [Water Solubility ]
12mg/L at 20℃ | [Major Application]
pharmaceutical (small molecule) | [InChI]
InChI=1S/C22H19N3O6/c26-19-13-30-10-9-23(19)14-5-7-15(8-6-14)24-11-16(31-22(24)29)12-25-20(27)17-3-1-2-4-18(17)21(25)28/h1-8,16H,9-13H2/t16-/m1/s1 | [InChIKey]
KUQNYAUTIWQAKY-MRXNPFEDSA-N | [SMILES]
C1(=O)C2=C(C=CC=C2)C(=O)N1C[C@@H]1OC(=O)N(C2=CC=C(N3CCOCC3=O)C=C2)C1 | [LogP]
-0.2 at 25℃ |
| Questions And Answer | Back Directory | [Uses]
1H-isoindole-1,3(2H)-dione, 2-[[(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]- is an important intermediate for the synthesis of rivaroxaban, which is an anticoagulant and the first orally active direct factor Xa inhibitor.
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| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Flammability and Explosibility]
Nonflammable | [Synthesis]
The general procedure for the synthesis of 2-[[(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-1H-isoindole-1,3(2H)-dione from 4-(3-oxomorpholinyl)phenyl isocyanate and (S)-2-(ethoxylen-2-ylmethyl)isoindoline-1,3-dione was as follows: the (S)- 2-(oxiran-2-ylmethyl)isoindoline-1,3-dione (4.56 g, 22.46 mmol, 1.3 eq.) and 4-(4-isocyanatophenyl)morpholin-3-one (3.77 g, 17.29 mmol) were dissolved in isoamyl acetate (70 mL), respectively. The reaction mixture was heated to 120 °C, followed by the addition of magnesium chloride (0.12 g, 1.28 mmol). After the reaction lasted for 4 h, a white solid product (6.97 g, 95.5% yield) was obtained by filtration. The product was confirmed by mass spectrometry by ESI-MS (m/z): 422 (M + H), 444 (M + Na); 1H NMR (400 MHz, CDCl3) δ: 3.74 (m, 2H), 3.94 (m, 4H), 4.10 (m, 2H), 4.32 (s, 2H), 4.98 (m, 1H), 7.34 (d, 2H), and 7.56 (d, 2H), 7.75 (m, 2H), 7.88 (m, 2H) were characterized by NMR; HPLC purity was 98.82%. | [References]
[1] Patent: EP2837628, 2015, A1. Location in patent: Paragraph 0029
[2] Patent: US2015/38704, 2015, A1. Location in patent: Paragraph 0048-0051 |
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