(6S,7R)-2-amino-6-(propylamino)-4,5,6,7-tetrahydro-1,3-benzothiazol-7-ol

• ChemBase ID: 171137
• Molecular Formular: C10H17N3OS
• Molecular Mass: 227.32648
• Monoisotopic Mass: 227.10923318
• SMILES: [C@H]1([C@H](CCc2c1sc(n2)N)NCCC)O
• Canonical SMILES: CCCN[C@H]1CCc2c([C@@H]1O)sc(n2)N
• InChI: InChI=1S/C10H17N3OS/c1-2-5-12-6-3-4-7-9(8(6)14)15-10(11)13-7/h6,8,12,14H,2-5H2,1H3,(H2,11,13)/t6-,8+/m0/s1
• InChIKey: UWNDKVURLHPSSG-POYBYMJQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6S,7R)-2-amino-6-(propylamino)-4,5,6,7-tetrahydro-1,3-benzothiazol-7-ol
• IUPAC Traditional name: (6S,7R)-2-amino-6-(propylamino)-4,5,6,7-tetrahydro-1,3-benzothiazol-7-ol
• Synonyms: (6S,7R)-2-Amino-4,5,6,7-tetrahydro-6-(propylamino)-7-benzothiazolol; rac-trans-7-Hydroxy Pramipexole

Database IDs

• PubChem SID: 164227047
• PubChem CID: 71749272

CALCULATED PROPERTIES

• Acid pKa: 13.420597
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -2.3508625
• LogD (pH = 7.4): -1.3373287
• Log P: 0.8452865
• Molar Refractivity: 60.8643 cm^3
• Polarizability: 23.484268 Å^3
• Polar Surface Area: 71.17 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 140-142°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H952145

Pramipexole derivative used for the preparation of (S)-Pramipexole via resolution of 2,6-diamino-7-hydroxy-4,5,6,7-tetrahydrobenzothiazole derivatives.

REFERENCES

• Validation of a column liquid chromatographic method for the analysis of pramipexole and its 5 impurities. Journal of AOAC International (2010)
• 93(2010)
• 1102-1112. Gegoe, Csaba Lehel; Fejes, Imre; Garaczi, Sandor; Kovacs, Imre; Lukacs, Ferenc; Majerc