ethyl 3-[2-(dimethylamino)ethyl]-5-{[(4S)-2-oxo-1,3-oxazolidin-4-yl]methyl}-1H-indole-2-carboxylate hydrochloride

• ChemBase ID: 179660
• Molecular Formular: C19H26ClN3O4
• Molecular Mass: 395.88044
• Monoisotopic Mass: 395.16118401
• SMILES: Cl.O1C[C@@H](NC1=O)Cc1cc2c(cc1)[nH]c(c2CCN(C)C)C(=O)OCC
• Canonical SMILES: CCOC(=O)c1[nH]c2c(c1CCN(C)C)cc(cc2)C[C@H]1COC(=O)N1.Cl
• InChI: InChI=1S/C19H25N3O4.ClH/c1-4-25-18(23)17-14(7-8-22(2)3)15-10-12(5-6-16(15)21-17)9-13-11-26-19(24)20-13;/h5-6,10,13,21H,4,7-9,11H2,1-3H3,(H,20,24);1H/t13-;/m0./s1
• InChIKey: GGMZETZRWDUKSC-ZOWNYOTGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 3-[2-(dimethylamino)ethyl]-5-{[(4S)-2-oxo-1,3-oxazolidin-4-yl]methyl}-1H-indole-2-carboxylate hydrochloride
• IUPAC Traditional name: ethyl 3-[2-(dimethylamino)ethyl]-5-{[(4S)-2-oxo-1,3-oxazolidin-4-yl]methyl}-1H-indole-2-carboxylate hydrochloride
• Synonyms: 3-[2-(Dimethylamino)ethyl]-5-[[(4S)-2-oxo-4-oxazolidinyl]methyl]-1H-indole-2-carboxylic Acid Ethyl Ester Hydrochloride; (S)-3-(2-Dimethylaminoethyl)-5-(2-oxo-1,3- oxazolidin-4-ylmethyl)-1H-indol-2-carboxylic Acid Ethyl Ester Hydrochloride; Zolmitriptan 2-Carboxylic Acid Ethyl Ester Hydrochloride

Database IDs

• CAS Number: 868622-23-5
• PubChem SID: 164235570
• PubChem CID: 69794675

CALCULATED PROPERTIES

• Acid pKa: 12.025288
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.9761763
• LogD (pH = 7.4): 0.4973301
• Log P: 2.3231614
• Molar Refractivity: 99.0906 cm^3
• Polarizability: 39.153103 Å^3
• Polar Surface Area: 83.66 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - Z639015

Zolmitriptan (Z639000) impurity. Also, an intermediate used in the process for the preparation of Zolmitriptan compounds via Fischer indole synthesis.

REFERENCES

• Moloney, G., et al.: J. Med. Chem., 1997, 40, 2347 (1997)