3-AMINO-ISONICOTINIC ACID METHYL ESTER

Bezeichnung:3-AMINO-ISONICOTINIC ACID METHYL ESTER

CAS-Nr55279-30-6

Englisch Name:3-AMINO-ISONICOTINIC ACID METHYL ESTER

CBNumberCB2406062

SummenformelC7H8N2O2

Molgewicht152.15

MOL-Datei55279-30-6.mol

3-AMINO-ISONICOTINIC ACID METHYL ESTER physikalisch-chemischer Eigenschaften

Schmelzpunkt	84-86
Siedepunkt	292.5±20.0 °C(Predicted)
Dichte	1.238±0.06 g/cm3(Predicted)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Aggregatzustand	powder to crystal
pka	4.05±0.18(Predicted)
Farbe	White to Yellow to Green
InChI	InChI=1S/C7H8N2O2/c1-11-7(10)5-2-3-9-4-6(5)8/h2-4H,8H2,1H3
InChIKey	XLQIGLBALJNHKR-UHFFFAOYSA-N
SMILES	C1=NC=CC(C(OC)=O)=C1N
CAS Datenbank	55279-30-6(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi,Xn
R-Sätze:	22-36/38
S-Sätze:	24/25
WGK Germany	WGK 3
Hazard Note	Irritant
HS Code	29333990
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral

Gefahreninformationscode (GHS)

3-AMINO-ISONICOTINIC ACID METHYL ESTER Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften
Yellow powder
Verwenden
3-Aminoisonicotinic Acid Methyl Ester is a useful synthetic intermediate. It is used in the synthesis of morpholinophenylquinazolines and related derivatives as PI3 kinase p110α inhibitors. It is also used to synthesize aryl tetrahydropyridine inhibitors of farnesyltransferase as antitumor agents.
Synthese

67-56-1

7579-20-6

55279-30-6

3-Aminoisonicotinic acid (3.55 g, 25.7 mmol) was added with concentrated sulfuric acid (2.5 ml) and methanol (50 ml), and the reaction was heated to reflux at 80°C for 3 days. After completion of the reaction, methanol was removed by evaporation and the residue was diluted with deionized water (75 ml) and heated to 80 °C. Solid sodium carbonate was added slowly until no gas was produced. The reaction mixture was cooled to room temperature and extracted with dichloromethane (2 x 100 ml). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated to give methyl 3-aminoisonicotinate as a beige solid (2.36 g, 60% yield). The product was characterized by 1H NMR (500 MHz, DMSO-d6): δ 8.24 (1H, s), 7.74 (1H, d, J=5.3 Hz), 7.46 (1H, d, J=5.2 Hz), 6.67 (2H, brs), 3.83 (3H, s). The mass spectrum (ES+) showed the molecular ion peak m/z 153 ([M+H]+).
Einzelnachweise
[1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 7, p. 1359 - 1362
[2] Patent: WO2005/49613, 2005, A1. Location in patent: Page/Page column 38
[3] Patent: WO2008/74749, 2008, A1. Location in patent: Page/Page column 62-63
[4] Chemical Communications, 2016, vol. 52, # 59, p. 9283 - 9286

3-AMINO-ISONICOTINIC ACID METHYL ESTER Upstream-Materialien And Downstream Produkte

3-AMINO-ISONICOTINIC ACID METHYL ESTER Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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