Velusetrag

Base Information

• Chemical Name: Velusetrag
• CAS No.: 866933-46-2
• Molecular Formula: C₂₅H₃₆N₄O₅S
• Molecular Weight: 504.651
• UNII: J4VNV64ARB
• ChEMBL ID: CHEMBL2087337
• DSSTox Substance ID: DTXSID001029768
• Metabolomics Workbench ID: 153642
• NCI Thesaurus Code: C84238
• Pharos Ligand ID: URJ4RRMSHKU8,URJNQB5XZRXP
• Wikidata: Q76422184
• Wikipedia: Velusetrag
• Mol file: 866933-46-2.mol

Synonyms:1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid ((1S,3R,5R)-8-((R)-2-hydroxy-3-(methanesulfonyl-methyl-amino)propyl)-8-aza-bicyclo(3.2.1)oct-3-yl)amide;TD-5108;TD5108;velusetrag

Chemical Property of Velusetrag

Chemical Property:

• PSA: 123.82000
• Density: 1.34
• LogP: 3.15340
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 504.24064144
• Heavy Atom Count: 35
• Complexity: 932

Purity/Quality:

97% ^*data from raw suppliers

1,2-Dihydro-N-[(3-endo)-8-[(2R)-2-hydroxy-3-[methyl(methylsulfonyl)amino]propyl]-8-azabicyclo[3.2.1]oct-3-yl]-1-(1-methylethyl)-2-oxo-3-quinolinecarboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)N1C2=CC=CC=C2C=C(C1=O)C(=O)NC3CC4CCC(C3)N4CC(CN(C)S(=O)(=O)C)O
• Isomeric SMILES: CC(C)N1C2=CC=CC=C2C=C(C1=O)C(=O)NC3C[C@H]4CC[C@@H](C3)N4C[C@H](CN(C)S(=O)(=O)C)O
• Recent ClinicalTrials: Velusetrag for the Treatment of Chronic Intestinal Pseudo-Obstruction (CIPO).
• Recent EU Clinical Trials: Velusetrag for the treatment of Chronic Intestinal Pseudo-Obstruction (CIPO). A multicenter double-blind, placebo-controlled, cross-over, multiple (n=1) trial.

Technology Process of Velusetrag

There total 15 articles about Velusetrag 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:

1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid {(1S,3R,5R)-8-aza-bicyclo[3.2.1]oct-3-yl}amide trifluoroacetate (866777-83-5) + N-methyl-N-[(S)-2-oxiran-2-ylmethyl]methanesulfonamide (866777-98-2) → Velusetrag (866933-46-2)

Guidance literature:

1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid {(1S,3R,5R)-8-aza-bicyclo[3.2.1]oct-3-yl}amide trifluoroacetate; With sodium hydroxide; In ethanol; water; at 20 ℃; for 0.5h;

N-methyl-N-[(S)-2-oxiran-2-ylmethyl]methanesulfonamide; In ethanol; water; for 2h; Heating / reflux;

Reference yield:

N-Boc-nortropinone (185099-67-6) → Velusetrag (866933-46-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: ammonium formate / palladium 10% on activated carbon / methanol; water / 72 h

2.1: sodium hydroxide / water; toluene / 0.17 h / 5 - 20 °C

2.2: 0.5 h / 3 - 5 °C

3.1: trifluoroacetic acid / water / 2.83 h / 20 °C

4.1: tert-butyl methyl ether / 2 h / 1 - 2 °C

5.1: sodium hydroxide / ethanol; water / 0.5 h / 20 °C

5.2: 2 h / Heating / reflux

With sodium hydroxide; ammonium formate; trifluoroacetic acid; palladium 10% on activated carbon; In methanol; ethanol; tert-butyl methyl ether; water; toluene;

Reference yield:

acetonedicarboxylic acid (542-05-2) → Velusetrag (866933-46-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: cis,trans-2,5-dimethoxytetrahydrofuran; hydrogenchloride / water / 0.33 h / 0 °C

2.1: methanol / 0 - 20 °C

3.1: hydrogen / palladium(II) hydroxide/carbon / ethyl acetate / 48 h / 3102.97 Torr

4.1: ammonium formate / palladium 10% on activated carbon / methanol; water / 72 h

5.1: sodium hydroxide / water; toluene / 0.17 h / 5 - 20 °C

5.2: 0.5 h / 3 - 5 °C

6.1: trifluoroacetic acid / water / 2.83 h / 20 °C

7.1: tert-butyl methyl ether / 2 h / 1 - 2 °C

8.1: sodium hydroxide / ethanol; water / 0.5 h / 20 °C

8.2: 2 h / Heating / reflux

With cis,trans-2,5-dimethoxytetrahydrofuran; hydrogenchloride; sodium hydroxide; hydrogen; ammonium formate; trifluoroacetic acid; palladium(II) hydroxide/carbon; palladium 10% on activated carbon; In methanol; ethanol; tert-butyl methyl ether; water; ethyl acetate; toluene;

upstream raw materials:

1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid {(1S,3R,5R)-8-aza-bicyclo[3.2.1]oct-3-yl}amide trifluoroacetate

N-methyl-N-[(S)-2-oxiran-2-ylmethyl]methanesulfonamide

((R)-2-hydroxy-3-{3-[(1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carbonyl)amino]-(1S,3R,5R)-8-azabicyclo[3.2.1]oct-8-yl}propyl)methylcarbamic acid tert-butyl ester

methanesulfonyl chloride

Refernces

• 1、 -. "Prokinetic agent for bowel preparation". Page/Page column 6. . Retrieved 2008/12/09.