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

Bezeichnung:1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one

CAS-Nr55314-16-4

Englisch Name:1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one

CBNumberCB1406106

SummenformelC10H12N2O

Molgewicht176.22

MOL-Datei55314-16-4.mol

1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one physikalisch-chemischer Eigenschaften

Schmelzpunkt	86-88
Siedepunkt	281.4±36.0 °C(Predicted)
Dichte	1.070±0.06 g/cm3(Predicted)
Dampfdruck	0.049Pa at 20℃
storage temp.	Inert atmosphere,Room Temperature
Löslichkeit	Soluble in chloroform and dichloromethane.
Aggregatzustand	powder to crystal
pka	6.19±0.70(Predicted)
Farbe	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
Oberflächenspannung	71.8mN/m at 1.008g/L and 20℃
CAS Datenbank	55314-16-4(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi,Xn
R-Sätze:	22-36/37/38
S-Sätze:	26-36/37/39
HazardClass	IRRITANT
HS Code	29333990

Gefahreninformationscode (GHS)

1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
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.
Chemische Eigenschaften
Off-White Solid
Verwenden
3-Dimethylamino-1-(3-pyridyl)-2-propen-1-one is used ads pharmaceutical intermediate, an imatinib intermediate.
Verwenden
Rasagiline intermediate
Synthese

350-03-8

4637-24-5

55314-16-4

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.
Einzelnachweise
[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 Upstream-Materialien And Downstream Produkte

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