1H-1,4-Diazepine, hexahydro-1-(5-isoquinolinylsulfonyl)-,monohydrochloride

Base Information

• Chemical Name: 1H-1,4-Diazepine, hexahydro-1-(5-isoquinolinylsulfonyl)-,monohydrochloride
• CAS No.: 105628-07-7
• Molecular Formula: C14H18ClN3O2S
• Molecular Weight: 327.835
• Hs Code.: 29339900
• Pharos Ligand ID: PR7RKZVNN5TC
• Mol file: 105628-07-7.mol

Synonyms:AKOS026750641;1H-1,4-Diazepine, hexahydro-1-(5-isoquinolinylsulfonyl)-,monohydrochloride

Chemical Property of 1H-1,4-Diazepine, hexahydro-1-(5-isoquinolinylsulfonyl)-,monohydrochloride

Chemical Property:

• Appearance/Colour: white solid
• Melting Point: 220.5°; mp 219.3° (Shirotani)
• Boiling Point: 506.2 °C at 760 mmHg
• Flash Point: 259.9 °C
• PSA: 70.68000
• LogP: 4.17030
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: H2O: >200 mg/mL
• Water Solubility.: Soluble in water and dimethyl sulfoxide. Insoluble in ethanol.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 327.0808257
• Heavy Atom Count: 21
• Complexity: 421

Purity/Quality:

99% ^*data from raw suppliers

HA1077 ^*data from reagent suppliers

Safty Information:

• Statements: 22
• Safety Statements: 36-60

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [H+].C1CNCCN(C1)S(=O)(=O)C2=CC=CC3=C2C=CN=C3.[Cl-]
• Description: Fasudil hydrochloride, a novel calcium antagonistic vasodilator, was marketed for the treatment of cerebral vasospasm following subarachnoid hemorrhage (SAH). Fasudil is also a potent inhibitor of myosin light chain kinase and protein kinase C. In contrast to other calcium channel blockers, which regulate the influx of calcium ions through the cell membrane but not involved in the intracellular regulatory mechanism of the calcium, fasudil was suggested to have an intracellular mode of action in relaxing vascular smooth muscle. In patients with neurological deficits due to vasospasm, fasudil decreased the occurrence of angiographic severe and symptomatic vasospasm and cerebral infarction without decreasing systemic blood pressure. Fasudil is reportedly in clinical trials for acute ischemic stroke, sequelae of cerebral vascular diseases and angina pectoris.
• Uses: Fasudil monohydrochloride is used in the prevention and treating cardiovascular and cerebrovascular diseases. It is also used in the inhibition of proliferation of vascular smooth muscle cells. It serves as a selective Rho-associated protein kinase (ROCK) inhibitor. Further, it protects against methyl mercury-induced axonal degeneration. vasodilator, potent Rho-kinase inhibitor

Technology Process of 1H-1,4-Diazepine, hexahydro-1-(5-isoquinolinylsulfonyl)-,monohydrochloride

There total 21 articles about 1H-1,4-Diazepine, hexahydro-1-(5-isoquinolinylsulfonyl)-,monohydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

1,4-Diazacycloheptane (505-66-8) + isoquinoline-5-sulfonyl chloride hydrochloride (105627-79-0) → fasudil hydrochloride (105628-07-7,133337-43-6,203911-27-7)

Guidance literature:

In dichloromethane; at 0 - 50 ℃; for 2h; Temperature;

Reference yield: 84.4%

1,4-Diazacycloheptane (505-66-8) + isoquinoline-5-sulfonic acid (27655-40-9) + 1-chloro-3,5-dimethoxybenzene (7051-16-3) → fasudil hydrochloride (105628-07-7,133337-43-6,203911-27-7)

Guidance literature:

isoquinoline-5-sulfonic acid; 1-chloro-3,5-dimethoxybenzene; With 4-methyl-morpholine; In chloroform; at 10 ℃; for 4h; Reflux;

1,4-Diazacycloheptane; In chloroform; at 30 ℃; for 3.5h; Reagent/catalyst; Solvent; Further stages; Reflux;

Reference yield: 78.1%

C14H18ClN3O2S → fasudil hydrochloride (105628-07-7,133337-43-6,203911-27-7)

Guidance literature:

C₁₄H₁₈ClN₃O₂S; With tetrabutylammomium bromide; potassium iodide; sodium hydroxide; In methanol; Reflux; Large scale;

With hydrogenchloride; In ethanol; at 0 - 5 ℃; pH=5.5 - 6; Large scale;

DOI:10.1021/acs.oprd.1c00211

upstream raw materials:

1,4-Diazacycloheptane

5-isoquinolinesulfonyl chloride

fasudil

isoquinoline-5-sulfonic acid

Downstream raw materials:

fasudil

Refernces

• 1、 -. "Preparation method of compound fasudil hydrochloride". Paragraph 0036; 0054-0055. . Retrieved 2021/09/11.
• 2、 -. "Method for preparing isoquinoline hydrochloride intermediate and Rho kinase inhibitor by using BTC/Ph3PO chlorination system". Paragraph 0112-0127. . Retrieved 2020/11/23.