Sildenafil Chlorosulfonyl Chemical Properties

Melting point:

180-182°C

Density 

1.48±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly, Heated)

form 

Solid

pka

9.87±0.20(Predicted)

color 

White to Pale Beige

Stability:

Moisture Sensitive

InChI

InChI=1S/C17H19ClN4O4S/c1-4-6-12-14-15(22(3)21-12)17(23)20-16(19-14)11-9-10(27(18,24)25)7-8-13(11)26-5-2/h7-9H,4-6H2,1-3H3,(H,19,20,23)

InChIKey

RVVOSOSBFSYZDM-UHFFFAOYSA-N

SMILES

C1(S(Cl)(=O)=O)=CC=C(OCC)C(C2NC(=O)C3N(C)N=C(CCC)C=3N=2)=C1

CAS DataBase Reference

139756-22-2

Safety Information

HS Code 

2933599590

Sildenafil Chlorosulfonyl Usage And Synthesis

Description

Sildenafil chlorosulfonyl is a synthetic intermediate in the synthesis of the phosphodiesterase 5 (PDE5) inhibitor sildenafil. It is also a potential impurity found in commercial preparations of sildenafil.

Chemical Properties

Off-White Solid

Uses

The compound Sildenafil Chlorosulfonyl Impurity (139756-22-2) is a derivative of Sildenafil. It is widely used in the treatment of pulmonary hypertension as it is capable of inhibiting cGMP and acts as a potent selective inhibitor of PDE5.

Synthesis

Example 1 Preparation of 5-(2-ethoxy-5-chlorosulfonyl)phenyl-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one: Chlorosulfuric acid (50 mL) was added to a 100 mL three-neck flask and placed in an ice bath. Under stirring, 5-(2-ethoxy)phenyl-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (31.2 g, 0.1 mol) was added in batches. The reaction was exothermic and stirred continuously for 12 hours. Upon completion of the reaction, the reaction solution was slowly poured into ice water (100 g) and a white solid precipitated. The solid was collected by filtration and dried to give a white solid product (30 g) in 76% yield.

References

[1] Journal of Medicinal Chemistry, 2008, vol. 51, # 9, p. 2807 - 2815
[2] Angewandte Chemie - International Edition, 2017, vol. 56, # 1, p. 221 - 224
[3] Angew. Chem., 2017, vol. 129, # 1, p. 227 - 230,4
[4] Chemical Communications, 2016, vol. 52, # 67, p. 10245 - 10248
[5] Patent: EP2666776, 2013, A1. Location in patent: Paragraph 0022; 0023

Sildenafil Chlorosulfonyl(139756-22-2)Related Product Information

• Tofacitinib citrate
• 7H-Pyrazolo[4,3-d]pyrimidin-7-one, 5-(5-chloro-2-ethoxyphenyl)-1,6-dihydro-1-methyl-3-propyl-
• KF31327
• 5-CHLOROSULFONYL-2-ETHOXYBENZOIC ACID
• 2-ETHOXY-5-[(4-METHYLPIPERAZIN-1-YL)SULFONYL]BENZOIC ACID
• 1-Piperazinesulfonicacid,4-methyl-(9CI)
• Lidocaine Impurity
• MONOETHYLGLYCINEXYLIDIDE
• Nor Lidocaine Hydrochloride
• N-(2,6-DIMETHYLPHENYL)-2-(METHYLAMINO)ACETAMIDE HYDROCHLORIDE
• Methisosildenafil impure
• Acotiamide Impurity
• Terazosin EP Impurity O
• Methisosildenafil Impurity
• 7,8-Dihydro-14-hydroxy- normorphinone
• Methyl 2-(2-hydroxy-4,5-diMethoxybenzaMido)thiazole-4-carboxylate
• Donepezil Impurity
• 3,5-Dimethyl-piperazine-1-carboxylic acid tert-butyl ester