5-[N-(TERT-BUTOXYCARBONYL)AMINO]-2-CHLOROPYRIDINE Chemical Properties

Melting point:

127-129°C

Boiling point:

283.7±25.0 °C(Predicted)

Density 

1.245±0.06 g/cm3(Predicted)

storage temp. 

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

pka

12.06±0.70(Predicted)

Appearance

Light brown to light purple Solid

InChI

InChI=1S/C10H13ClN2O2/c1-10(2,3)15-9(14)13-7-4-5-8(11)12-6-7/h4-6H,1-3H3,(H,13,14)

InChIKey

IRHNQVINMHHEIO-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NC1=CC=C(Cl)N=C1

Safety Information

HazardClass 

IRRITANT

HS Code 

29333990

5-[N-(TERT-BUTOXYCARBONYL)AMINO]-2-CHLOROPYRIDINE Usage And Synthesis

Synthesis

Step a: To a solution of dichloromethane (200 mL) containing 6-chloropyridin-3-amine (30.0 g, 0.23 mol), DMAP (1 g), and Et3N (41.7 g, 0.47 mol) was slowly added Boc2O (54.5 g, 0.25 mol) at 0 °C. The reaction mixture was gradually warmed to room temperature and stirred overnight. Upon completion of the reaction, the reaction mixture was washed with saturated NaHCO3 solution. The aqueous phase was extracted with dichloromethane and the combined organic phases were washed with brine (100 mL) and dried over anhydrous Na2SO4. Concentration of the organic phase under reduced pressure afforded tert-butyl 6-chloropyridin-3-ylcarbamate (50.0 g, 94% yield), the product was used directly for the next reaction without further purification.1H NMR (300 MHz, CDCl3) δ 8.23 (d, J=2.7 Hz, 1H), 7.97 (d, J=6.9 Hz, 1H), 7.27-7.24 (m, 1H), 6.58 (m, 1H), 7.25 (m, 1H), 6.25 (m, 1H), 6.25 (m, 1H). 1H), 6.58 (s, 1H), 1.52 (s, 9H).

References

[1] Inorganic Chemistry, 2017, vol. 56, # 14, p. 8381 - 8389
[2] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 9, p. 1233 - 1236
[3] Patent: US2002/22624, 2002, A1
[4] Patent: US2009/253736, 2009, A1. Location in patent: Page/Page column 24
[5] Patent: US2007/249615, 2007, A1. Location in patent: Page/Page column 29; 31; 34

5-[N-(TERT-BUTOXYCARBONYL)AMINO]-2-CHLOROPYRIDINE(171178-45-3)Related Product Information

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