2-AMINO-4,7-DIHYDRO-5H-THIENO[2,3-C]PYRIDINE-3,6-DICARBOXYLIC ACID 6-TERT BUTYL ESTER 3-ETHYL ESTER Chemical Properties

Melting point:

153 °C

Boiling point:

492.5±45.0 °C(Predicted)

Density 

1.252±0.06 g/cm3(Predicted)

storage temp. 

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

pka

0.40±0.20(Predicted)

Appearance

Light yellow to yellow Solid

CAS DataBase Reference

193537-14-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/39

Hazard Note 

Irritant

HS Code 

2934999090

2-AMINO-4,7-DIHYDRO-5H-THIENO[2,3-C]PYRIDINE-3,6-DICARBOXYLIC ACID 6-TERT BUTYL ESTER 3-ETHYL ESTER Usage And Synthesis

Synthesis

General Steps: Step a. Synthesis of 2-amino-4,7-dihydro-5H-thieno[2,3-c]pyridine-3,6-dicarboxylic acid 6-tert-butyl 3-ethyl ester In anhydrous ethanol (50 mL), N-tert-butoxycarbonyl-4-piperidone (12.9 g), ethyl cyanoacetate (7.345 g), and sulfur powder (2.080 g) were mixed, followed by the addition of triethylamine (9 mL). The reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, the precipitate was collected by filtration and washed with ethanol to afford 2-amino-4,5-dihydrothieno[2,3-c]pyridine-3,6(7H)-dicarboxylic acid-6-tert-butyl ester (18.7 g, 88% yield). Product characterization data: 1H NMR (300 MHz, CDCl3): δ 6.02 (s, 2H), 4.31 (s, 2H), 4.23 (q, 2H, J = 7.2 Hz), 3.58 (t, 2H, J = 6.0 Hz), 2.72-2.80 (br s, 2H), 1.44 (s, 9H), 1.30 (t, 3H, J = 7.2 Hz). LC-MS (ESI) m/z: 327.0 (M + H)+.

References

[1] Synlett, 2010, # 9, p. 1351 - 1354
[2] Patent: US2010/120805, 2010, A1. Location in patent: Page/Page column 44
[3] Journal of Medicinal Chemistry, 2010, vol. 53, # 20, p. 7316 - 7326
[4] Patent: WO2009/33581, 2009, A1. Location in patent: Page/Page column 62
[5] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3101 - 3112

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