ethyl (2R,4S)-2-ethyl-4-[(methoxycarbonyl)amino]-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinoline-1-carboxylate

• ChemBase ID: 168622
• Molecular Formular: C17H21F3N2O4
• Molecular Mass: 374.3548496
• Monoisotopic Mass: 374.14534182
• SMILES: c1c(cc2c(c1)N([C@@H](C[C@@H]2NC(=O)OC)CC)C(=O)OCC)C(F)(F)F
• Canonical SMILES: CCOC(=O)N1[C@H](CC)C[C@@H](c2c1ccc(c2)C(F)(F)F)NC(=O)OC
• InChI: InChI=1S/C17H21F3N2O4/c1-4-11-9-13(21-15(23)25-3)12-8-10(17(18,19)20)6-7-14(12)22(11)16(24)26-5-2/h6-8,11,13H,4-5,9H2,1-3H3,(H,21,23)/t11-,13+/m1/s1
• InChIKey: SEYVRRKNFKPZAE-YPMHNXCESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2R,4S)-2-ethyl-4-[(methoxycarbonyl)amino]-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinoline-1-carboxylate
• IUPAC Traditional name: ethyl (2R,4S)-2-ethyl-4-[(methoxycarbonyl)amino]-6-(trifluoromethyl)-3,4-dihydro-2H-quinoline-1-carboxylate
• Synonyms: (2R,4S)-2-Ethyl-3,4-dihydro-4-[(methoxycarbonyl)amino]-6-(trifluoromethyl)-1(2H)-quinolinecarboxylic Acid Ethyl Ester; (2R,4S)-2-Ethyl-4-methoxycarbonylamino-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic Acid Ethyl Ester

Database IDs

• CAS Number: 474645-94-8
• PubChem SID: 162262754
• PubChem CID: 10126361

CALCULATED PROPERTIES

• Acid pKa: 12.468137
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.380175
• LogD (pH = 7.4): 3.380172
• Log P: 3.3801754
• Molar Refractivity: 87.433 cm^3
• Polarizability: 33.055107 Å^3
• Polar Surface Area: 67.87 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

DETAILS

Toronto Research Chemicals - E921990

Torcetrapib intermediate.

REFERENCES

• Hamashima, Y., et al.: Chem. Pharm. Bull., 54, 1351 (2006)
• Kidd, J., et al.: Nat. Rev. Drug Discov., 5, 813 (2006)