1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one Chemical Properties

Melting point:

86-88

Boiling point:

281.4±36.0 °C(Predicted)

Density 

1.070±0.06 g/cm3(Predicted)

vapor pressure 

0.049Pa at 20℃

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Soluble in chloroform and dichloromethane.

form 

powder to crystal

pka

6.19±0.70(Predicted)

color 

Light yellow to Brown

InChI

InChI=1S/C10H12N2O/c1-12(2)7-5-10(13)9-4-3-6-11-8-9/h3-8H,1-2H3

InChIKey

MZLRFUCMBQWLNV-FNORWQNLSA-N

SMILES

C(C1=CC=CN=C1)(=O)C=CN(C)C

LogP

0.26 at 20℃ and pH7.2

Surface tension

71.8mN/m at 1.008g/L and 20℃

CAS DataBase Reference

55314-16-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

29333990

1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one Usage And Synthesis

Description

1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one can be used in the synthesis of imatinib and nilotinib (AMN107), a compound currently in multiple Phase II/III clinical trials for chronic granulocytic leukaemia. Imatinib, on the other hand, is a cancer growth blocker known as a tyrosine kinase inhibitor (TKI), which is used to treat a wide range of leukaemias, myelodysplastic/myeloproliferative disorders, systemic mastocytosis, eosinophilia syndromes, raised dermal fibrosarcoma and gastrointestinal mesenchymal tumours.

Chemical Properties

Off-White Solid

Uses

Rasagiline intermediate

Uses

3-Dimethylamino-1-(3-pyridyl)-2-propen-1-one is used ads pharmaceutical intermediate, an imatinib intermediate.

Synthesis

Example-2: Preparation of 3-dimethylamino-1-pyridin-3-ylacrylone A: 3-acetylpyridine (25 g, 0.20 mol), N,N-dimethylformamide dimethyl acetal (37 g, 0.31 mol) and acetic acid (2.5 mL) were mixed and heated to react for 2 hrs at 90-95°C while successive removal of methanol generated. Upon completion of the reaction, the excess methanol in the reaction was removed by distillation under reduced pressure. The reaction mixture was diluted with water and extracted with dichloromethane (125 mL). The organic layer was washed with water and subsequently concentrated to dryness under reduced pressure to afford 34 g (92% yield) of 1-(3-pyridinyl)-3-(dimethylamino)-2-propen-1-one with a purity of 99.1% by HPLC analysis.

Solubility in organics

1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one is soluble in Chloroform and Dichloromethane.

References

[1] Synlett, 2016, vol. 27, # 15, p. 2233 - 2236
[2] RSC Advances, 2018, vol. 8, # 47, p. 26828 - 26836
[3] Molecules, 2009, vol. 14, # 10, p. 4166 - 4179
[4] Patent: WO2011/39782, 2011, A1. Location in patent: Page/Page column 14
[5] Organic Process Research and Development, 2008, vol. 12, # 3, p. 490 - 495

1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one(55314-16-4)Related Product Information

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