1(2H)-Phthalazinone, 4-((4-chlorophenyl)methyl)-2-(((2R)-1-(4-(4-(3-(hexahydro-1H-azepin-1-yl)propoxy)phenyl)butyl)-2-pyrrolidinyl)methyl)-

Base Information

• Chemical Name: 1(2H)-Phthalazinone, 4-((4-chlorophenyl)methyl)-2-(((2R)-1-(4-(4-(3-(hexahydro-1H-azepin-1-yl)propoxy)phenyl)butyl)-2-pyrrolidinyl)methyl)-
• CAS No.: 955359-72-5
• Molecular Formula: C₃₉H₄₉ClN₄O₂
• Molecular Weight: 641.297
• UNII: S08212J4ZR
• ChEMBL ID: CHEMBL1767164
• Metabolomics Workbench ID: 153724
• Pharos Ligand ID: XH4NFD8QGT63
• Wikidata: Q27288388
• Mol file: 955359-72-5.mol

Synonyms:GSK 1004723;GSK-1004723;GSK1004723

Chemical Property of 1(2H)-Phthalazinone, 4-((4-chlorophenyl)methyl)-2-(((2R)-1-(4-(4-(3-(hexahydro-1H-azepin-1-yl)propoxy)phenyl)butyl)-2-pyrrolidinyl)methyl)-

Chemical Property:

• XLogP3: 8.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 14
• Exact Mass: 640.3544045
• Heavy Atom Count: 46
• Complexity: 938

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CCCN(CC1)CCCOC2=CC=C(C=C2)CCCCN3CCCC3CN4C(=O)C5=CC=CC=C5C(=N4)CC6=CC=C(C=C6)Cl
• Isomeric SMILES: C1CCCN(CC1)CCCOC2=CC=C(C=C2)CCCCN3CCC[C@@H]3CN4C(=O)C5=CC=CC=C5C(=N4)CC6=CC=C(C=C6)Cl
• Recent ClinicalTrials: Single and Repeat Dose First Time in Human Study for an Intranasal H1/H3 Dual Antagonist in Healthy Male Subjects
• Recent EU Clinical Trials: A randomised, double-blind, placebo-controlled 4-period crossover study to assess the efficacy and safety of repeat dose intranasal GSK1004723 (1000μg), oral GSK835726 (10mg) and cetirizine (10mg) in the environmental challenge chamber in subjects with seasonal allergic rhinitis

Technology Process of 1(2H)-Phthalazinone, 4-((4-chlorophenyl)methyl)-2-(((2R)-1-(4-(4-(3-(hexahydro-1H-azepin-1-yl)propoxy)phenyl)butyl)-2-pyrrolidinyl)methyl)-

There total 18 articles about 1(2H)-Phthalazinone, 4-((4-chlorophenyl)methyl)-2-(((2R)-1-(4-(4-(3-(hexahydro-1H-azepin-1-yl)propoxy)phenyl)butyl)-2-pyrrolidinyl)methyl)- 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: 83.0%

hexamethylene imine (111-49-9) + 4-[(4-chlorophenyl)methyl]-2-[((2R)-1-{4-[4-(3-chloropropoxy)phenyl]butyl}-2-pyrrolidinyl)methyl]-1(2H)-phthalazinone (955360-35-7) → GSK-1004723 (955359-72-5)

Guidance literature:

With potassium carbonate; potassium iodide; In 4-methyl-2-pentanone; for 18h; Product distribution / selectivity; Heating / reflux;

Reference yield: 35.0%

4-[(4-chlorophenyl)methyl]-2-{[(2R)-2-pyrrolidinyl]methyl}-1(2H)-phthalazinone (955359-79-2) + 4-(4-{[3-(hexahydro-1H-azepin-1-yl)propyl]oxy}phenyl)butyl methanesulfonate (955360-05-1) → GSK-1004723 (955359-72-5)

Guidance literature:

With sodium hydrogencarbonate; In acetonitrile; at 80 ℃; for 120h; Inert atmosphere;

DOI:10.1021/jm1013874

Reference yield:

4-(4-[3-(hexahydro-1H-azepin-1-yl)propoxy]phenyl)-3-butyn-1-ol (955360-03-9) → GSK-1004723 (955359-72-5)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / methanol; ethanol / 4 h

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C

3: sodium hydrogencarbonate / acetonitrile / 120 h / 80 °C / Inert atmosphere

With hydrogenchloride; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; In methanol; ethanol; dichloromethane; acetonitrile;

DOI:10.1021/jm1013874

upstream raw materials:

hexamethylene imine

4-[(4-chlorophenyl)methyl]-2-[((2R)-1-{4-[4-(3-chloropropoxy)phenyl]butyl}-2-pyrrolidinyl)methyl]-1(2H)-phthalazinone

4-[(4-chlorophenyl)methyl]-2-{[(2R)-2-pyrrolidinyl]methyl}-1(2H)-phthalazinone

4-(4-{[3-(hexahydro-1H-azepin-1-yl)propyl]oxy}phenyl)butyl methanesulfonate