6-((3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy)-N-methyl-3-pyridinecarboxamide

Base Information

• Chemical Name: 6-((3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy)-N-methyl-3-pyridinecarboxamide
• CAS No.: 720690-73-3
• Deprecated CAS: 854485-15-7
• Molecular Formula: C21H25N3O2
• Molecular Weight: 351.448
• UNII: 5T4TX6CO53
• DSSTox Substance ID: DTXSID801005982
• Wikipedia: GSK-189254
• Wikidata: Q5514566
• Pharos Ligand ID: FJD2F2X1Z6U4
• ChEMBL ID: CHEMBL517140
• Mol file: 720690-73-3.mol

Synonyms:6-((3-cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy)-N-methyl-3-pyridinecarboxamide;GSK 189254;GSK-189254;GSK189254

Chemical Property of 6-((3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy)-N-methyl-3-pyridinecarboxamide

Chemical Property:

• Boiling Point: 545.0±50.0 °C(Predicted)
• PKA: 14.26±0.46(Predicted)
• PSA: 57.95000
• Density: 1.195±0.06 g/cm3(Predicted)
• LogP: 3.69930
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 351.19467705
• Heavy Atom Count: 26
• Complexity: 482

Purity/Quality:

99%, ^*data from raw suppliers

GSK189254A >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC(=O)C1=CN=C(C=C1)OC2=CC3=C(CCN(CC3)C4CCC4)C=C2
• Recent ClinicalTrials: A Study Of GSK189254 And Duloxetine In The Electrical Hyperalgesia Model Of Healthy Volunteers
• Recent EU Clinical Trials: An open label, dose escalation study with a double blind randomised placebo controlled withdrawal to examine the effects of the histamine H3 antagonist GSK189254 in patients with narcolepsy.
• Description: GSK189254A is a histamine H3 receptor antagonist for the treatment of narcolepsy.It may also be useful for the treatment of dementia and neuropathic pain. Its pharmacological effect may be related to its effect on increasing the release neurotransmitter in the brain. Microdialysis studies demonstrated that GSK189254 increased the release of acetylcholine, noradrenaline, and dopamine in the anterior cingulate cortex and acetylcholine in the dorsal hippocampus. GSK189254 significantly improved performance of rats in diverse cognition paradigms, including passive avoidance, water maze, object recognition, and attentional set shift. These data suggest that GSK189254 may have therapeutic potential for the symptomatic treatment of dementia in Alzheimer's disease and other cognitive disorders.

Technology Process of 6-((3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy)-N-methyl-3-pyridinecarboxamide

There total 17 articles about 6-((3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy)-N-methyl-3-pyridinecarboxamide 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: 66.0%

3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol (720689-55-4) + 6-chloro-N-methylnicotinamide (54189-82-1) → 6-[(3-cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-N-methyl-3-pyridinecarboxamide (720690-73-3)

Guidance literature:

3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol; With sodium hydride; In dimethyl sulfoxide; mineral oil; for 0.5h;

6-chloro-N-methylnicotinamide; In dimethyl sulfoxide; mineral oil; at 120 ℃;

DOI:10.1016/j.bmcl.2012.05.076

Reference yield:

N-methyl-6-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yloxy)-3-pyridinecarboxamide (720692-49-9) + cyclobutanone (1191-95-3) → 6-[(3-cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-N-methyl-3-pyridinecarboxamide (720690-73-3)

Guidance literature:

N-methyl-6-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yloxy)-3-pyridinecarboxamide; cyclobutanone; With acetic acid; In dichloromethane; at 20 ℃; for 1h;

With sodium tris(acetoxy)borohydride; In dichloromethane; at 0 - 20 ℃; for 16h;

With sodium hydroxide; In dichloromethane; water; for 0.5h;

Reference yield:

3-(tert-butyloxycarbonyl)-7-hydroxy-2,3,4,5-tetrahydro-1H-3-benzazepine (149354-10-9) → 6-[(3-cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-N-methyl-3-pyridinecarboxamide (720690-73-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium tert-butylate / tert-butyl alcohol / 0.5 h / 20 °C

1.2: 20 h / Heating / reflux

2.1: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C

3.1: acetic acid / dichloromethane / 1 h / 20 °C

3.2: 16 h / 0 - 20 °C

3.3: 0.5 h

With hydrogenchloride; potassium tert-butylate; acetic acid; In 1,4-dioxane; dichloromethane; tert-butyl alcohol;

upstream raw materials:

6-chloro-N-methylnicotinamide

N-methyl-6-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yloxy)-3-pyridinecarboxamide

cyclobutanone

3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol

Downstream raw materials:

[3H]-GSK₁₈₉₂₅₄

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