4-PYRIDIN-4-YL-THIAZOL-2-YLAMINE Chemical Properties

Melting point:

270-272 °C

Boiling point:

378.9±17.0 °C(Predicted)

Density 

1.333±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMF: 5 mg/ml; DMSO: 10 mg/ml; DMSO:PBS (pH 7.2) (1:10): 0.1 mg/ml; Ethanol: 0.14 mg/ml

form 

A crystalline solid

pka

2.89±0.10(Predicted)

Sensitive 

Air Sensitive

CAS DataBase Reference

30235-28-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-41-22

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

2934100090

4-PYRIDIN-4-YL-THIAZOL-2-YLAMINE Usage And Synthesis

Uses

4-PYRIDIN-4-YL-THIAZOL-2-YLAMINE is a synthetic intermediate useful for pharmaceutical synthesis.

Synthesis

General procedure for the synthesis of 4-(pyridin-4-yl)thiazol-2-amines from 4-(bromoacetyl)pyridine hydrobromide and thiourea: Synthesis of batch 1: A mixture of 4-(bromoacetyl)pyridine hydrobromide (2.21 g, 7.90 mmol) and thiourea (0.60 g, 7.90 mmol) in anhydrous ethanol (10 mL) was subjected to stirring in a Biotage microwave reactor at 100°C for 30 min. After completion of the reaction, it was cooled to room temperature, the solid precipitate was collected by filtration and dried under vacuum. Synthesis of batch 2: A mixture of 4-(bromoacetyl)pyridine hydrobromide (2.54 g, 9.06 mmol) and thiourea (0.69 g, 9.06 mmol) in anhydrous ethanol (10 mL) was placed in a Biotage microwave reactor and the reaction was stirred for 30 minutes at 100°C. The reaction was cooled to room temperature and the solid precipitate was collected by filtration. After completion of the reaction, it was cooled to room temperature, the solid precipitate was collected by filtration and dried under vacuum. Synthesis of batch 3: A mixture of 4-(bromoacetyl)pyridine hydrobromide (2.16 g, 7.73 mmol) and thiourea (0.58 g, 7.73 mmol) in anhydrous ethanol (10 mL) was placed in a Biotage microwave reactor and the reaction was stirred for 30 minutes at 100°C. The reaction was cooled to room temperature and the solid precipitate was collected by filtration. After completion of the reaction, it was cooled to room temperature, the solid precipitate was collected by filtration and dried under vacuum. The products of batches 1, 2 and 3 were combined and suspended in saturated aqueous sodium bicarbonate solution. Filtered, washed with sodium bicarbonate solution and dried under vacuum to afford the title compound 4-(pyridin-4-yl)thiazol-2-amine as a pale pink solid (5.53 g, 31.27 mmol, 95% yield).1H NMR (400 MHz, CD3OD) δ 8.49 (d, J = 6.3 Hz, 2H), 7.79 (d, J = 6.3 Hz, 2H) , 7.25 (s, 1H).

References

[1] MedChemComm, 2012, vol. 3, # 6, p. 699 - 709
[2] Patent: WO2011/130740, 2011, A2. Location in patent: Page/Page column 42
[3] Patent: WO2012/125981, 2012, A2. Location in patent: Page/Page column 131
[4] Journal of Medicinal Chemistry, 2010, vol. 53, # 2, p. 787 - 797
[5] Patent: WO2009/114552, 2009, A1. Location in patent: Page/Page column 133

4-PYRIDIN-4-YL-THIAZOL-2-YLAMINE(30235-28-0)Related Product Information

• 4-(2-METHYL-IMIDAZO[1,2-A ]PYRIDIN-3-YL)-THIAZOL-2-YLAMINE
• 2-PYRIDIN-4-YL-THIAZOL-4-YLAMINE
• 4-(6-BROMO-2-METHYL-IMIDAZO[1,2-A]PYRIDIN-3-YL)-THIAZOL-2-YLAMINE
• 4-PYRIDIN-3-YL-THIAZOL-2-YLAMINE
• 4-PYRIDIN-4-YL-THIAZOL-2-YLAMINE
• 5-METHYL-4-PYRIDIN-4-YL-THIAZOL-2-YLAMINE
• 4-(6-CHLORO-PYRIDIN-3-YL)-THIAZOL-2-YLAMINE
• 4-PYRIDIN-2-YL-THIAZOL-2-YLAMINE
• 4-(2,6-DIMETHYL-IMIDAZO[1,2-A]PYRIDIN-3-YL)-THIAZOL-2-YLAMINE
• 4-(6-CHLORO-2-METHYL-IMIDAZO[1,2-A]PYRIDIN-3-YL)-THIAZOL-2-YLAMINE
• N-(4-PYRIDIN-4-YL-1,3-THIAZOL-2-YL)BENZENE-1,4-DIAMINE
• 4-(2-METHYL-6-NITRO-IMIDAZO[1,2-A]PYRIDIN-3-YL)-THIAZOL-2-YLAMINE
• 4-(6,8-DIBROMO-2-METHYL-IMIDAZO[1,2-A]PYRIDIN-3-YL)-THIAZOL-2-YLAMINE
• 4-(2,7-DIMETHYL-IMIDAZO[1,2-A]PYRIDIN-3-YL)-THIAZOL-2-YLAMINE
• 2-(4-PYRIDIN-4-YL-1,3-THIAZOL-2-YL)-3-(TRIFLUOROMETHYL)-2,3,3A,4-TETRAHYDROCHROMENO[4,3-C]PYRAZOL-3-OL
• 2-(4-PYRIDIN-4-YL-1,3-THIAZOL-2-YL)-3-(TRIFLUOROMETHYL)-4,5-DIHYDRO-2H-BENZO[G]INDAZOLE
• 2-CYANO-N-(4-PYRIDIN-4-YL-1,3-THIAZOL-2-YL)ACETAMIDE
• N-(4-PYRIDIN-4-YL-1,3-THIAZOL-2-YL)BENZENE-1,4-DIAMINE HYDROBROMIDE