trans-N-(1-Acetyl-2,3-dihydro-1H-indol-6-yl)-3-(3-cyanophenyl)-N-(1-(2-cyclopentylethyl)piperidin-4-yl)acrylamide

Base Information

• Chemical Name: trans-N-(1-Acetyl-2,3-dihydro-1H-indol-6-yl)-3-(3-cyanophenyl)-N-(1-(2-cyclopentylethyl)piperidin-4-yl)acrylamide
• CAS No.: 683746-68-1
• Deprecated CAS: 685854-91-5
• Molecular Formula: C₃₂H₃₈N₄O₂
• Molecular Weight: 510.679
• UNII: OW44B6FA0Y
• DSSTox Substance ID: DTXSID60438082
• Nikkaji Number: J2.792.962A
• Wikidata: Q27893043
• Pharos Ligand ID: X8L7YR5H1A3L
• ChEMBL ID: CHEMBL21283
• Mol file: 683746-68-1.mol

Synonyms:JNJ-5207787;N-(1-Acetyl-2,3-dihydro-1H-indol-6-yl)-3-(3-cyano-phenyl)-N-(1-(2-cyclopentyl-ethyl)-piperidin-4yl)acrylamide

Chemical Property of trans-N-(1-Acetyl-2,3-dihydro-1H-indol-6-yl)-3-(3-cyanophenyl)-N-(1-(2-cyclopentylethyl)piperidin-4-yl)acrylamide

Chemical Property:

• Density: 1.22
• Storage Temp.: Store at RT
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 510.29947647
• Heavy Atom Count: 38
• Complexity: 894

Purity/Quality:

97% ^*data from raw suppliers

JNJ5207787 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)N1CCC2=C1C=C(C=C2)N(C3CCN(CC3)CCC4CCCC4)C(=O)C=CC5=CC(=CC=C5)C#N
• Isomeric SMILES: CC(=O)N1CCC2=C1C=C(C=C2)N(C3CCN(CC3)CCC4CCCC4)C(=O)/C=C/C5=CC(=CC=C5)C#N
• Description: JNJ-5207787 is an antagonist of the neuropeptide Y (NPY) receptor Y2 that blocks peptide YY binding (IC50 = 100 nM). It displays 100-fold selectivity for Y2 over other NPY receptors and has minimal effect on a panel of 50 receptors, ion channels, and transporters, except for sodium channel 2. JNJ-5207787 is intraperitoneally bioavailable and brain penetrant in rats, occupying maximally 50% of Y2 receptor binding sites in the hypothalamic area.
• Uses: JNJ 5207787 is a small molecule antagonist of the neuropeptide Y Y2 receptor.

Technology Process of trans-N-(1-Acetyl-2,3-dihydro-1H-indol-6-yl)-3-(3-cyanophenyl)-N-(1-(2-cyclopentylethyl)piperidin-4-yl)acrylamide

There total 6 articles about trans-N-(1-Acetyl-2,3-dihydro-1H-indol-6-yl)-3-(3-cyanophenyl)-N-(1-(2-cyclopentylethyl)piperidin-4-yl)acrylamide 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: 71.0%

trans-N-(1-acetyl-2,3-dihydro-1H-indol-6-yl)-3-(3-cyanophenyl)-N-piperidin-4-yl-acrylamide (1207279-96-6) + sodium 2-cyclopentyl-1-hydroxyethanesulfonate (84803-66-7) → trans-N-(1-acetyl-2,3-dihydro-1H-indol-6-yl)-3-(3-cyanophenyl)-N-[1-(2-cyclopentylethyl)piperidin-4-yl]acrylamide (683746-68-1)

Guidance literature:

sodium 2-cyclopentyl-1-hydroxyethanesulfonate; With triethylamine; In 1,2-dichloro-ethane; at 20 ℃; for 0.166667h; Inert atmosphere; Molecular sieve;

trans-N-(1-acetyl-2,3-dihydro-1H-indol-6-yl)-3-(3-cyanophenyl)-N-piperidin-4-yl-acrylamide; In 1,2-dichloro-ethane; at 20 ℃; for 0.666667h; Inert atmosphere;

With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20 ℃; Inert atmosphere;

DOI:10.1055/s-0029-1217050

Reference yield: 50.0%

(3E)-3-(3-cyanophenyl)acrylic acid (16642-93-6) → trans-N-(1-acetyl-2,3-dihydro-1H-indol-6-yl)-3-(3-cyanophenyl)-N-[1-(2-cyclopentylethyl)piperidin-4-yl]acrylamide (683746-68-1)

Guidance literature:

Reference yield:

1-acetyl-6-aminoindoline (62368-29-0) → trans-N-(1-acetyl-2,3-dihydro-1H-indol-6-yl)-3-(3-cyanophenyl)-N-[1-(2-cyclopentylethyl)piperidin-4-yl]acrylamide (683746-68-1)

Guidance literature:

Multi-step reaction with 2 steps

1: Na(OAc)3BH / 1,2-dichloro-ethane

2: Et₃N / CH₂Cl₂

With sodium tris(acetoxy)borohydride; triethylamine; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1016/j.bmcl.2003.12.057

upstream raw materials:

trans 3-(3-cyanophenyl)-2-propenoic acid chloride

1-acetyl-6-aminoindoline

(3E)-3-(3-cyanophenyl)acrylic acid

trans-N-(1-acetyl-2,3-dihydro-1H-indol-6-yl)-3-(3-cyanophenyl)-N-piperidin-4-yl-acrylamide

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