| Identification | Back Directory | [Name]
N-(4-CYANO-PHENYL)-GLYCINE | [CAS]
42288-26-6 | [Synonyms]
4-Cyano phenyl Glycine
N-(4-Cynophenyl)-Glycine
N-(p-Cyanophenyl)glycine
Dabigatran Intermediate 2
N-(4-CYANO-PHENYL)-GLYCIN
N-(4-CYANO-PHENYL)-GLYCINE
Glycine, N-(4-cyanophenyl)-
N-(4-Cyanophenyl)glycine >
N-(4-Cyanophenyl)glycine(DG10)
N-(4-Cyanophenyl)glycine
Dabigatran Impurity 2 (DABRC-02)
[(4-Cyanophenyl)aMino]acetic Acid
Dabigatran Etexilate Intermediate 2
Dabigatran pharMaceutical interMediate
4-(((Carboxy)Methyl)aMino)benzonitrile
N-(4-Cyanophenyl)glycine CAS:42288-26-6
Pradaxa mesylate intermediates，N-(4-cyanophenyl)-Glycine | [EINECS(EC#)]
459-560-3 | [Molecular Formula]
C9H8N2O2 | [MDL Number]
MFCD01464022 | [MOL File]
42288-26-6.mol | [Molecular Weight]
176.172 |
| Questions And Answer | Back Directory | [Description]
Dabigatran etexilate is a novel synthetic direct thrombin inhibitor, a prodrug of dabigatran, a non-peptide thrombin inhibitor. Dabigatran etexilate intermediate II is an impurity produced during the preparation of dabigatran etexilate. | [Physical properties]
N-(4-Cyanophenyl)glycine is a off-white Solid. |
| Chemical Properties | Back Directory | [Melting point ]
237 °C(dec.) | [Boiling point ]
447.2±30.0 °C(Predicted) | [density ]
1.30±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
Dichloromethane (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
3.81±0.10(Predicted) | [color ]
White to Pale Yellow | [InChI]
InChI=1S/C9H8N2O2/c10-5-7-1-3-8(4-2-7)11-6-9(12)13/h1-4,11H,6H2,(H,12,13) | [InChIKey]
KJRQMXRCZULRHF-UHFFFAOYSA-N | [SMILES]
C(O)(=O)CNC1=CC=C(C#N)C=C1 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white Solid | [Uses]
Dabigatran etexilate intermediate | [Synthesis]
3.2.3 Preparation of [(4-cyanophenyl)amino]acetic acid (V). Molecular formula: C9H8N2O2. molecular weight: 176.17. Raw materials: 90g (0.75mol) of bromoacetic acid (F), 211.7g (1.5mol) of p-aminobenzonitrile (G), 35g (0.42mol) of sodium bicarbonate. Procedure: bromoacetic acid (F) and p-aminobenzonitrile (G) were mixed in 1250 ml of water to form a suspension. The suspension was placed in a bath heated to 100-110°C for 3 hours. Upon completion of the reaction, the reaction vessel was removed from the bath and cooled to room temperature, followed by further cooling in a refrigerator. The precipitate was separated by diafiltration and dried in a vacuum desiccator at 100 °C. Yield of crude product: 122 g (92.8% yield), HPLC purity: 97%. Purification step: the crude product was converted to sodium salt and re-acidified using aqueous sodium bicarbonate to release the free acid by dilute hydrochloric acid (1:1). After filtration, the product was washed with water and dried in a vacuum desiccator at 105°C. The product was then purified to a sodium salt using aqueous sodium bicarbonate. Yield of purified product: 115 g (88% yield), HPLC purity: 99.1%, water content: 0.13%, sulfated ash: 1.8%. | [References]
[1] Patent: WO2009/111997, 2009, A1. Location in patent: Page/Page column 11
[2] Patent: WO2013/111163, 2013, A2. Location in patent: Page/Page column 18
[3] Patent: US2015/11589, 2015, A1. Location in patent: Paragraph 0121-0122
[4] European Journal of Medicinal Chemistry, 2016, vol. 120, p. 148 - 159 |
|
|