3-[(3-AMINO-4-METHYLAMINO-BENZOYL)-PYRIDIN-2-YL-AMINO]-PROPIONIC ACID ETHYL ESTER Chemical Properties

Melting point:

104.0 to 108.0 °C

Boiling point:

576.2±50.0 °C(Predicted)

Density 

1.261±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

5.37±0.11(Predicted)

color 

Off-White to Pale Beige

InChI

InChI=1S/C18H22N4O3/c1-3-25-17(23)9-11-22(16-6-4-5-10-21-16)18(24)13-7-8-15(20-2)14(19)12-13/h4-8,10,12,20H,3,9,11,19H2,1-2H3

InChIKey

PCPATNZTKBOKOY-UHFFFAOYSA-N

SMILES

N(C1N=CC=CC=1)(CCC(=O)OCC)C(C1C=CC(NC)=C(N)C=1)=O

LogP

1.37 at 20℃

Safety Information

HS Code 

2933.39.9200

3-[(3-AMINO-4-METHYLAMINO-BENZOYL)-PYRIDIN-2-YL-AMINO]-PROPIONIC ACID ETHYL ESTER Usage And Synthesis

Uses

Alzheimer's disease therapeutic, Co Q10 analog, antioxidant

Uses

Ethyl 3-(3-amino-4-(methylamino)-N-(pyridin-2-yl)benzamido)propanoate is the impurity of Dabigatran (D100090), which is a nonpeptide, direct thrombin inhibitor and is antithrombotic.

Synthesis

(D) Preparation of Intermediate VI: In a hydrogenation reactor, 43 g of ethyl 3-(4-(methylamino)-3-nitro-N-(pyridin-2-yl)benzoylamino)propionate and 4.7 g of nickel Nguyenne catalyst were added. 4 mL of tetrahydrofuran was added as solvent and three nitrogen substitutions were performed to remove air. The reaction mixture was then stirred under hydrogen atmosphere and heated to 60°C. The reaction process was monitored by thin layer chromatography (TLC). After completion of the reaction, a filtration operation was carried out and the filter cake was washed with a small amount of tetrahydrofuran. The filter cake was recovered and disposed properly. The filtrate was dried over anhydrous sodium sulfate, diafiltrated again and finally concentrated to dryness under reduced pressure to give 38.3 g of intermediate VI (6) in 96% yield.

References

[1] Patent: CN104031031, 2017, B. Location in patent: Paragraph 0028; 0033; 0035; 0040; 0042; 0047
[2] Patent: WO2007/71742, 2007, A1. Location in patent: Page/Page column 22-23
[3] Patent: WO2007/71743, 2007, A1. Location in patent: Page/Page column 18
[4] Patent: CN105461688, 2016, A. Location in patent: Paragraph 0043; 0044
[5] Patent: WO2007/71742, 2007, A1. Location in patent: Page/Page column 22

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