| Identification | Back Directory | [Name]
(2R,3S,4R,5R)-2-(hydroxyMethyl)-5-(6-((2-(Methylthio)ethyl)aMino)-2-((3,3,3-trifluoropropyl)thio)-9H-purin-9-yl)tetrahydrofuran-3,4-diol | [CAS]
163706-58-9 | [Synonyms]
Cangrelor inter
Cangrelor Intermediate
Cangrelor Intermediates
Cangrelor Metabolite (Cangrelor Impurity 3)
N6-(2-Methylthioethyl)-2-(3,3,3-trifluoropropylthio)adenosine
N-[2-(Methylthio)ethyl]-2-[(3,3,3-trifluoropropyl)thio]adenosine
Adenosine, N-[2-(Methylthio)ethyl]-2-[(3,3,3-trifluoropropyl)thio]- (9CI)
(2R,3S,4R,5R)-2-(hydroxyMethyl)-5-(6-((2-(Methylthio)ethyl)aMino)-2-((3,3,3-trifluoropropyl)thio)-9H-purin-9-yl)
((3aR,4R,6R,6aR)-6-(6-amino-2-((3,3,3-trifluoropropyl)thio)-9H- purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol
(2R,3S,4R,5R)-2-(hydroxyMethyl)-5-(6-((2-(Methylthio)ethyl)aMino)-2-((3,3,3-trifluoropropyl)thio)-9H-purin-9-yl)tetrahydrofuran-3,4-diol
(2R,3S,4R,5R)-2-(Hydroxymethyl)-5-(6-((2-(methylthio)ethyl)amino)-2-((3,3,3-trifluoropropyl)thio)-9H-purin-9-yl)tetrahydrofuran-3,4-diol Cangrelor Intermediate
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-((2-(methylthio)ethyl)amino)-2- ((3,3,3-trifluoropropyl)thio)-9H-purin-9-yl)tetrahydrofuran-3,4-diol N6-(2-Methylthioethyl)-2-(3,3,3-trifluoropropylthio)adenosine | [EINECS(EC#)]
812-944-8 | [Molecular Formula]
C16H22F3N5O4S2 | [MDL Number]
MFCD15832982 | [MOL File]
163706-58-9.mol | [Molecular Weight]
469.5 |
| Chemical Properties | Back Directory | [Melting point ]
179-181°C | [Boiling point ]
747.5±70.0 °C(Predicted) | [density ]
1.70±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,2-8°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
13.08±0.70(Predicted) | [color ]
White to Light Yellow | [InChIKey]
ZGVUPMJCZYBIDI-IDTAVKCVSA-N | [SMILES]
OC[C@H]1O[C@@H](N2C3C(=C(N=C(SCCC(F)(F)F)N=3)NCCSC)N=C2)[C@H](O)[C@@H]1O |
| Hazard Information | Back Directory | [Uses]
N-?[2-?(Methylthio)?ethyl]?-?2-?[(3,?3,?3-?trifluoropropyl)?thio]?-adenosine is used for developing platelet P2T receptor antagonists, which have potential applications for antithrombotic therapy. | [Synthesis]
The general procedure for the synthesis of (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-((2-(methylthio)ethyl)amino)-2-((3,3,3-trifluoropropyl)thio)-9H-purin-9-yl)tetrahydrofuran-3,4-diol, using the compound (CAS:163706-57-8) as a raw material, is as follows: the crude obtained in Example 38 was reacted with the crude product (60.3 g) was co-dissolved with potassium carbonate (199 g, 1.44 mol) in 600 mL of isopropanol, heated to reflux and the reaction was maintained for 2 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to give a concentrate. To the concentrate, 300 mL of water was added and the pH was adjusted to about 7 using acetic acid with continuous stirring for 0.5 hours. Subsequently, the reaction mixture was filtered and the solid product was collected and dried to give a final 33.8 g of pale yellow solid product. The overall yield of this three-step synthetic process was 75% (based on the compound of formula (10)) and the product purity was 97.9% as analyzed by high performance liquid chromatography (HPLC). | [References]
[1] Patent: CN107973798, 2018, A. Location in patent: Paragraph 0259; 0264; 0265-0267; 0270; 0273
[2] Journal of Medicinal Chemistry, 1999, vol. 42, # 2, p. 213 - 220
[3] Patent: CN107973832, 2018, A. Location in patent: Paragraph 0028; 0253-0270 |
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