3-PYRIDINAMINE, 6-(1-METHYLETHYL)- Chemical Properties

Boiling point:

255.1±20.0 °C(Predicted)

Density 

1.008±0.06 g/cm3(Predicted)

storage temp. 

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

pka

6.77±0.10(Predicted)

Appearance

Light yellow to brown Liquid

InChI

InChI=1S/C8H12N2/c1-6(2)8-4-3-7(9)5-10-8/h3-6H,9H2,1-2H3

InChIKey

XYGFISRAXLLACA-UHFFFAOYSA-N

SMILES

C1=NC(C(C)C)=CC=C1N

Safety Information

HS Code 

2933399990

3-PYRIDINAMINE, 6-(1-METHYLETHYL)- Usage And Synthesis

Uses

6-Isopropylpyridin-3-amine is used to prepare quinolinonecarboxamides as modulators of ATP-binding cassette transporters.

Synthesis

General procedure for the synthesis of 3-amino-6-isopropylpyridine from 2-isopropyl-5-nitropyridine: 2-isopropyl-5-nitropyridine (1.30 g, 7.82 mmol) was dissolved in methanol (20 mL) and Raney Ni catalyst (0.25 g) was added. The reaction mixture was stirred for 2 hours at room temperature under hydrogen (1 atm) atmosphere. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to afford 2-isopropyl-5-aminopyridine (E-9) (0.55 g, 52% yield). The product was characterized by 1H NMR (CDCl3): δ 8.05 (s, 1H), 6.93-6.99 (m, 2H), 3.47 (br s, 2H), 2.92-3.02 (m, 1H), 1.24-1.26 (m, 6H).ESI-MS showed the molecular ion peak at 137.2 m/z (MH+).

References

[1] Patent: US2011/98311, 2011, A1
[2] Patent: US2012/309758, 2012, A1
[3] Patent: US2015/231142, 2015, A1. Location in patent: Paragraph 0700

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