5-[(TERT-BUTOXYCARBONYL)AMINO]-2-CHLOROISONICOTINIC ACID Chemical Properties

Boiling point:

420.6±45.0 °C(Predicted)

Density 

1.390±0.06 g/cm3(Predicted)

storage temp. 

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

pka

2.52±0.36(Predicted)

Appearance

White to off-white Solid

Safety Information

Risk Statements 

20/21/22

Safety Statements 

36/37-24/25

HazardClass 

IRRITANT

HS Code 

29333990

5-[(TERT-BUTOXYCARBONYL)AMINO]-2-CHLOROISONICOTINIC ACID Usage And Synthesis

Chemical Properties

Off-white solid

Synthesis

Step (c): Synthesis of 5-tert-butoxycarbonylamino-2-chloropyridine-4-carboxylic acid Tert-butyl 6-chloropyridin-3-ylcarbamate (800 mL ether suspension) was mixed with TMEDA and cooled to -75 °C. A hexane solution of 1.6 M n-butyllithium was slowly added dropwise at a temperature below -65 °C. After the dropwise addition was completed, the reaction mixture was warmed to -15°C to -10°C and stirred in this temperature range for 2 hours. Subsequently, the mixture was cooled again to -75°C and dry carbon dioxide gas was passed into it for 3 hours. Afterwards, the reaction mixture was allowed to slowly warm up to room temperature overnight, during which time carbon dioxide was continuously passed through. Upon completion of the reaction, the reaction was carefully quenched with 20% aqueous ammonium hydroxide solution (1.8 L) and the aqueous phase was extracted with ether. The reaction was then acidified to pH 5 with 50% aqueous hydrochloric acid, the resulting solid was collected by filtration, washed with water and dried to afford 33.07 g (69.3% yield) of 5-tert-butoxycarbonylamino-2-chloropyridine-4-carboxylic acid as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm: 1.5 (s, 9H), 7.7 (s, 1H), 9.1 (s, 1H), 10.0 (s, 1H). MS (APCI) m/z: [M + 1]+ = 273.1.

References

[1] Patent: WO2005/16926, 2005, A1. Location in patent: Page/Page column 114-115
[2] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 3, p. 256 - 261
[3] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 11, p. 1401 - 1405
[4] Patent: WO2005/16926, 2005, A1. Location in patent: Page/Page column 122-123
[5] Journal of the Chemical Society - Perkin Transactions 1, 1996, # 18, p. 2221 - 2226

5-[(TERT-BUTOXYCARBONYL)AMINO]-2-CHLOROISONICOTINIC ACID(171178-46-4)Related Product Information

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