3-{[(2R,3S)-2-{1-[3,5-bis(trifluoromethyl)phenyl](1,2-2H2)ethoxy}-3-(4-fluorophenyl)morpholin-4-yl](13C)methyl}-4,5-dihydro(3-13C)-1H-1,2,4-triazol-5-one

• ChemBase ID: 160771
• Molecular Formular: C23H21F7N4O3
• Molecular Mass: 536.41197208
• Monoisotopic Mass: 536.15689777
• SMILES: N1(CCO[C@@H]([C@@H]1c1ccc(cc1)F)OC(c1cc(cc(c1)C(F)(F)F)C(F)(F)F)C)[13CH2][13c]1[nH]c(=O)[nH]n1
• Canonical SMILES: Fc1ccc(cc1)[C@H]1[C@H](OCCN1[13CH2][13c]1n[nH]c(=O)[nH]1)OC(c1cc(cc(c1)C(F)(F)F)C(F)(F)F)C
• InChI: InChI=1S/C23H21F7N4O3/c1-12(14-8-15(22(25,26)27)10-16(9-14)23(28,29)30)37-20-19(13-2-4-17(24)5-3-13)34(6-7-36-20)11-18-31-21(35)33-32-18/h2-5,8-10,12,19-20H,6-7,11H2,1H3,(H2,31,32,33,35)/t12?,19-,20+/m0/s1/i11+1,18+1
• InChIKey: ATALOFNDEOCMKK-QUMWUUJASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[(2R,3S)-2-{1-[3,5-bis(trifluoromethyl)phenyl](1,2-^2H₂)ethoxy}-3-(4-fluorophenyl)morpholin-4-yl](^1^3C)methyl}-4,5-dihydro(3-^1^3C)-1H-1,2,4-triazol-5-one
• IUPAC Traditional name: 5-{[(2R,3S)-2-{1-[3,5-bis(trifluoromethyl)phenyl](1,2-^2H₂)ethoxy}-3-(4-fluorophenyl)morpholin-4-yl](^1^3C)methyl}-2,4-dihydro(5-^1^3C)-1,2,4-triazol-3-one
• Synonyms: 5-[[(2R,3S)-2-[(1R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-1,2-dihydro-3H-1,2,4-triazol-3-one-13C2,d2; Emend-13C2,d2; MK-0869-13C2,d2; Aprepitant-13C2,d2 (Major)

Database IDs

• PubChem SID: 162254906
• PubChem CID: 71313474

CALCULATED PROPERTIES

• Acid pKa: 9.646593
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 5.211254
• LogD (pH = 7.4): 5.2134037
• Log P: 5.215729
• Molar Refractivity: 116.9282 cm^3
• Polarizability: 43.31651 Å^3
• Polar Surface Area: 75.19 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 244-246°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A729802

This product is deuterated at the 1 position and on the ajacent methyl. The 1 position is the benylic position of the bis(trifluoromethyl) phenyl. This compound has a mixture of 1 to 4 deuterium atoms, there is no detectable unlabeled material.Aprepitan

REFERENCES

• Majumdar, A.K., et al.: J. Clin. Pharmacol., 46, 291 (1998)
• Hale, J.J., et al.: J. Med. Chem., 41, 4607 (1998)
• Campos, D., et al.: J. Clin. Oncol., 19, 1759 (1998)
• Van Belle, S., et al.: Cancer, 94, 3032 (1998)