N-(4-CYANO-PHENYL)-GLYCINE Chemical Properties

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

Safety Information

HS Code 

2926907090

N-(4-CYANO-PHENYL)-GLYCINE Usage And Synthesis

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.

Uses

Dabigatran etexilate intermediate

Uses

N-(4-Cyanophenyl)-glycine (cas# 42288-26-6) is a compound useful in organic synthesis.

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

N-(4-CYANO-PHENYL)-GLYCINE(42288-26-6)Related Product Information

• 3-(S)-(+)-(1-Carbamoyl-1,1-diphenylmethyl)pyrroloidine-L-(+)-tartarate
• HEXYL CHLOROFORMATE
• N-[[2-[[[4-(Aminoiminomethyl)phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-(2-pyridinyl)-beta-alanine ethyl ester hydrochloride
• 4-Aminobenzamidine dihydrochloride
• 3-[[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]pyridin-2-ylamino]propionic acid ethyl ester
• ETHYL N-[4-(METHYLAMINO)-3-NITROBENZOYL]-N-PYRIDIN-2-YL-SS-ALANINATE
• 3-[(3-AMINO-4-METHYLAMINO-BENZOYL)-PYRIDIN-2-YL-AMINO]-PROPIONIC ACID ETHYL ESTER
• 5-(2-Bromoethyl)-2,3-dihydrobenzofuran
• Dabigatran etexilate
• Dabigatran Etexilate Mesylate
• N-(4-CYANO-PHENYL)-GLYCINE
• (4-CYANO-PHENYLAMINO)-ACETIC ACID TERT-BUTYL ESTER
• ethyl 2-[(4-cyanophenyl)amino]acetate
• 1-(4-cyanophenyl)-4-hydroxypyrrolidine-2-carboxylic acid
• (S)-N-(4-CYANO-2-NITRO-PHENYL)-L-TYROSINE
• N-(4-Cyanophenyl)-L-proline
• methyl 2-[(4-cyanophenyl)(methyl)amino]acetate
• (3AR,4S,9BS)-8-CYANO-3A,4,5,9B-TETRAHYDRO-3H-CYCLOPENTA[C]QUINOLINE-4-CARBOXYLIC ACID