2-[(2R)-2-hydroxy-3-{[4-(3-oxomorpholin-4-yl)phenyl]amino}propyl]-2,3-dihydro-1H-isoindole-1,3-dione

• ChemBase ID: 171038
• Molecular Formular: C21H21N3O5
• Molecular Mass: 395.40854
• Monoisotopic Mass: 395.14812079
• SMILES: c1c(ccc(c1)N1C(=O)COCC1)NC[C@@H](O)CN1C(=O)c2c(C1=O)cccc2
• Canonical SMILES: O[C@@H](CN1C(=O)c2c(C1=O)cccc2)CNc1ccc(cc1)N1CCOCC1=O
• InChI: InChI=1S/C21H21N3O5/c25-16(12-24-20(27)17-3-1-2-4-18(17)21(24)28)11-22-14-5-7-15(8-6-14)23-9-10-29-13-19(23)26/h1-8,16,22,25H,9-13H2/t16-/m1/s1
• InChIKey: CKFVSMPWXAASIQ-MRXNPFEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2R)-2-hydroxy-3-{[4-(3-oxomorpholin-4-yl)phenyl]amino}propyl]-2,3-dihydro-1H-isoindole-1,3-dione
• IUPAC Traditional name: 2-[(2R)-2-hydroxy-3-{[4-(3-oxomorpholin-4-yl)phenyl]amino}propyl]isoindole-1,3-dione
• Synonyms: 2-[(2R)-2-Hydroxy-3-[[4-(3-oxo-4-morpholinyl)phenyl]amino]propyl]-1H-isoindole-1,3(2H)-dione; 4-[((2R)-Hydroxy-3-phthalimido)propylamine]phenyl-3-morpholinone

Database IDs

• CAS Number: 446292-07-5
• PubChem SID: 164226948
• PubChem CID: 11516758

CALCULATED PROPERTIES

• Acid pKa: 14.454773
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.30495396
• LogD (pH = 7.4): 0.31723422
• Log P: 0.31739312
• Molar Refractivity: 106.9201 cm^3
• Polarizability: 39.5973 Å^3
• Polar Surface Area: 99.18 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - H948920

Rivaroxaban intermediate.

REFERENCES

• Roehrig, S., et al.: J. Med. Chem., 48, 5900 (2005)