4-(4-cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione Chemical Properties

Boiling point:

435.2±38.0 °C(Predicted)

Density 

1.41±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

7.89±0.20(Predicted)

Appearance

White to off-white Powder

InChI

InChI=1S/C15H13N3S/c19-15-17-16-9-18(15)14-8-7-11(10-5-6-10)12-3-1-2-4-13(12)14/h1-4,7-10H,5-6H2,(H,17,19)

InChIKey

UFYFJMMSOUURSF-UHFFFAOYSA-N

SMILES

N1=CN(C2=C3C(C=CC=C3)=C(C3CC3)C=C2)C(=S)N1

CAS DataBase Reference

1533519-84-4

4-(4-cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione Usage And Synthesis

Chemical Properties

Off white powder

Uses

4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione is a reagent used in the discovery of Lesinurad, a HEK293 cell-based inhibitor.

Synthesis

Example 5. Preparation of 4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiols To a round-bottomed flask was added N-(4-cyclopropyl-1-naphthalenyl)-2-formylhydrazine thiocarboxamide (64.0 g, 225 mmol), N,N-dimethylformamide (300 mL), and 1 mol/L aqueous sodium hydroxide solution (225 mL) to form a mixture. After stirring, the mixture was heated to 30 °C and kept for 16 hours. After the reaction was completed, the mixture was cooled to room temperature (about 20°C). Subsequently, 1 mol/L hydrochloric acid (about 200 mL) was slowly added to the mixture until the pH of the mixture was about 6.0, and then water (about 500 mL) was added. The mixture was stirred for 15 minutes and then filtered. The filter cake was washed with water and the product was dried under vacuum at 50 °C for 5 h to give 4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol as a gray-green solid, 54.0 g in 90% yield. LC-MS: m/z (ESI): 268 (M + H)+. 1H NMR (400 MHz, acetone-d6): δ 8.57 (d, J = 8.0 Hz, 1H), 8.37 (s, 1H), 7.67 (m, 1H), 7.60 (m, 1H), 7.51 (d, J = 8.0 Hz, 1H), 7.48 (d, J = 8.0 Hz, 1H), 7.43 (d, J = 8.0 Hz, 1H), 2.50 (m, 1H), 1.16 (m, 2H), 0.84 (m, 2H).

References

[1] Patent: WO2014/198241, 2014, A1. Location in patent: Paragraph 069-070
[2] Patent: WO2014/8295, 2014, A1. Location in patent: Paragraph 0337

4-(4-cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione(1533519-84-4)Related Product Information

• Lesinurad Impurity B
• Lesinurad Impurity 5 Sodium Salt
• Lesinurad Impurity C1
• Lesinurad Impurity 2
• 3H-1,2,4-Triazole-3-thione, 5-amino-4-(4-cyclopropyl-1-naphthalenyl)-2,4-dihydro
• Lesinurad Impurity 4
• Lesinurad Impurity J
• Lesinurad Impurity 10
• 3-bromo-4-(4-cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione
• Lesinurad Impurity 22
• 4-cyclopropylnaphthalen-1-aMine hydrochloride
• Lesinurad Impurity A
• Methyl 2-(5-broMo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetate
• N-(4-Cyclopropyl-1-naphthalenyl)-2-formylhydrazinecarbothioamide
• Lesinurad Impurity N
• Lesinurad M4 Metabolite
• NAPHTHALENE, 1-CYCLOPROPYL-4-ISOTHIOCYANATO-
• lesinurad int