tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate Chemical Properties

Melting point:

42-44 °C(Solv: ethyl ether (60-29-7))

Boiling point:

390.9±42.0 °C(Predicted)

Density 

1.495±0.06 g/cm3(Predicted)

storage temp. 

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

pka

1.23±0.20(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C11H15BrN2O2S/c1-11(2,3)16-10(15)14-5-4-7-8(6-14)17-9(12)13-7/h4-6H2,1-3H3

InChIKey

RXXKNZKFRAFFOH-UHFFFAOYSA-N

SMILES

C1N(C(OC(C)(C)C)=O)CCC2N=C(Br)SC1=2

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN2811

HS Code 

2934100090

tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate Usage And Synthesis

Uses

2-Bromo-5-(tert-butoxycarbonyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine is a reagent used for the synthesis of tetrahydrothiazolopyridines, which are potent antagonists for the smoothened (smo) receptor.

Uses

2-Bromo-5-(tert-butoxycarbonyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine is a reagent used for the synthesis of tetrahydrothiazolopyridines, which are potent antagonists for the smoothened (smo) receptor.

Synthesis

Method G - Step e: Synthesis of tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate [0134] To a 100 mL DMF solution containing isoamyl nitrite (8.8 mL, 62.8 mmol) and copper(II) bromide (10.7 g, 48 mmol) was added tert-butyl 2-amino-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate (10 g, 39.2 mmol) at 0°C. The reaction was carried out at 40°C and the reaction mixture was purified. The reaction mixture was stirred at 40°C for 30 min and then concentrated by evaporation. The concentrate was dissolved in 50 mL of water and extracted with dichloromethane (100 mL × 2). The organic phases were combined, washed with brine (30 mL × 2), and dried over anhydrous sodium sulfate. Purification by silica gel column chromatography (eluent: dichloromethane) afforded the target product tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate (5.3 g, 42.4%) as a yellow solid.

References

[1] Heterocycles, 2004, vol. 63, # 7, p. 1555 - 1561
[2] Patent: WO2014/113191, 2014, A1. Location in patent: Paragraph 0133; 0134
[3] Patent: US2013/144061, 2013, A1. Location in patent: Paragraph 0244; 0245; 0246; 0247
[4] Journal of Medicinal Chemistry, 2014, vol. 57, # 9, p. 3687 - 3706
[5] Patent: WO2018/13774, 2018, A1. Location in patent: Page/Page column 309

tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate(365996-06-1)Related Product Information

• TERT-BUTYL 6,7-DIHYDROTHIAZOLO[5,4-C]PYRIDINE-5(4H)-CARBOXYLATE
• tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate