Isoquinoline-5-sulfonyl chloride hydrochloride

• CAS: 105627-79-0
• Catalog Number: ACM105627790
• Category: Main Products
• Molecular Weight: 264.13
• Molecular Formula: C9H7Cl2NO2S
• Synonyms: 5-Isoquinolinesulfonyl Chloride Hydrochloride
• Melting Point: 201-206 °C
• Appearance: White powder

Case Study

Isoquinoline-5-Sulfonyl Chloride Hydrochloride in The Synthesis Process of Fasudil Hydrochloride

Song M, et al. Journal of separation science, 2014, 37(7), 758-763.

Fasudil hydrochloride is a potent Rho kinase inhibitor and vasodilator. According to the basic principle of quality by design, relevant impurities in the production process of fasudil hydrochloride API were studied. Among them, isoquinoline-5-sulfonyl chloride hydrochloride is one of the important raw materials in the synthesis step of fasudil hydrochloride.
Origins of and approaches to eliminate impurities
· Impurity I was isoquinoline-5-sulfonic acid, the starting material of fasudil hydrochloride, which can be removed by recrystallization.
· Impurity II was formed by a side reaction of isoquinoline-5-sulfonic acid with thionyl chloride, which can be reduced by lowered reaction temperature.
· Impurity III was attributed to the double condensation reaction of homopiperazine with excess isoquinoline5-sulfonyl chloride during the synthesis, which can be eliminated by the control of starting materials ratio and the order of addition.
· The modified synthetic process: In the original synthetic processes, an equal molar amount of 1,4-diazepine was added dropwise into isoquinoline-5-sulfonyl chloride solution in which the sulfonyl chloride was always in excess. Subsequently, in order to reduce the possibility of the formation and to eliminate impurity III, isoquinoline-5-sulfonyl chloride solution was added slowly into 1,4-diazepine solution with stirring.

Isoquinoline-5-Sulfonyl Chloride Hydrochloride Used in the Synthesis of HIV-1 Integrase Inhibitors

Makhija M T, et al. Bioorganic & medicinal chemistry, 2004, 12(9), 2317-2333.

A series of compounds were designed and synthesized using a de novo drug design approach, and their potential as HIV-1 integrase inhibitors was explored. It involves the synthesis steps of isoquinoline-5-sulfonyl chloride hydrochloride and its further use in the synthesis of compound 4-7 in this work.
· Synthesis of isoquinoline-5-sulfonyl chloride hydrochloride (3)
A mixture of isoquinoline-5-sulfonic acid, 2 (4 g, 0.019 mol), thionyl chloride (25 mL), and dimethylformamide (0.1 mL) was refluxed for 2 h, and the excess thionyl chloride was distilled off in vacuo. The residue was suspended in dichloromethane, filtered, washed and dried to obtain crude crystalline isoquinoline-5-sulfonyl chloride hydrochloride.
· General procedure for the synthesis of compounds 4-7
To an ice cooled suspension of isoquinoline-5-sulfonyl chloride hydrochloride (5 g, 0.018 mol) in 20 mL dichloromethane, a mixture of substituted amine (0.018 mol) and pyridine (2.84 g, 0.036 mol) dissolved in 50 mL of dichloromethane was added in a dropwise manner with stirring over a period of 15 min. The reaction mixture was stirred for 1 h at 0-5 °C, and then at room temperature for 3-5 h. It was then washed with brine and dried over anhydrous sodium sulfate. The dried extract was evaporated to get the crude substituted isoquinoline-5-sulfonamide.

Custom Q&A

What is the molecular formula of isoquinoline-5-sulfonyl chloride hydrochloride?

The molecular formula is C9H7Cl2NO2S.

What is the molecular weight of isoquinoline-5-sulfonyl chloride hydrochloride?

The molecular weight is 264.13 g/mol.

How is isoquinoline-5-sulfonyl chloride hydrochloride represented in 2D structure?

The 2D structure can be viewed at the following link: https://pubchem.ncbi.nlm.nih.gov/image/imgsrv.fcgi?cid=13116932&t=s.

What are the synonyms of isoquinoline-5-sulfonyl chloride hydrochloride?

The synonyms include 105627-79-0, Isoquinoline-5-sulphonvl chloride hydrochloride, Isoquinoline-5-sulfonyl chloride HCl, and ISOQUINOLINE-5-SULFONYL CHLORIDE, HYDROCHLORIDE.

What is the IUPAC name of isoquinoline-5-sulfonyl chloride hydrochloride?

The IUPAC name is isoquinoline-5-sulfonyl chloride; hydrochloride.

What is the InChI key for isoquinoline-5-sulfonyl chloride hydrochloride?

The InChI key is GZQNTWHQJJVIAK-UHFFFAOYSA-N.

How many hydrogen bond donor counts does isoquinoline-5-sulfonyl chloride hydrochloride have?

It has 1 hydrogen bond donor count.

How many hydrogen bond acceptor counts does isoquinoline-5-sulfonyl chloride hydrochloride have?

It has 3 hydrogen bond acceptor counts.

What is the topological polar surface area of isoquinoline-5-sulfonyl chloride hydrochloride?

The topological polar surface area is 55.4Ų.

How many covalently-bonded units does isoquinoline-5-sulfonyl chloride hydrochloride have?

It has 2 covalently-bonded units.