(S,E)-3-(6-bromopyridin-2-yl)-2-cyano-N-(1-phenylbutyl)acrylamide

Base Information

• Chemical Name: (S,E)-3-(6-bromopyridin-2-yl)-2-cyano-N-(1-phenylbutyl)acrylamide
• CAS No.: 856243-80-6
• Molecular Formula: C19 H18 BrN3 O
• Molecular Weight: 384.275
• DSSTox Substance ID: DTXSID50459281
• Nikkaji Number: J3.264.508I
• Wikidata: Q72516581
• ChEMBL ID: CHEMBL1923233
• Mol file: 856243-80-6.mol

Synonyms:2-cyano-N-(1-phenylbutyl)-3-(6-bromopyridin-2-yl)acrylamide;degrasyn;WP1130

Chemical Property of (S,E)-3-(6-bromopyridin-2-yl)-2-cyano-N-(1-phenylbutyl)acrylamide

Chemical Property:

• PSA: 69.27000
• Density: 1.358
• LogP: 5.24898
• Storage Temp.: -20°
• Solubility.: Soluble in DMSO (up to 45 mg/ml), or in Ethanol (up to 25 mg/ml).
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 383.06332
• Heavy Atom Count: 24
• Complexity: 490

Purity/Quality:

98% min ^*data from raw suppliers

WP1130 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(C1=CC=CC=C1)NC(=O)C(=CC2=NC(=CC=C2)Br)C#N
• Isomeric SMILES: CCC[C@@H](C1=CC=CC=C1)NC(=O)/C(=C/C2=NC(=CC=C2)Br)/C#N
• Description: WP1130 (856243-80-6) is a novel DUB inhibitor directly inhibiting USP9x, USP5, USP14 and UCH37 inducing rapid accumulation of polyubiquitinated proteins. Triggers tumor cell apoptosis.1 Blocks Jak2 signaling via Jak2 ubiquitination.2 WP-1130 causes ablation of the oncogenic transcription factor ERG in prostate cancer cells.3 See methyl analog WP1066.

Technology Process of (S,E)-3-(6-bromopyridin-2-yl)-2-cyano-N-(1-phenylbutyl)acrylamide

There total 2 articles about (S,E)-3-(6-bromopyridin-2-yl)-2-cyano-N-(1-phenylbutyl)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: 65.0%

6-bromo-2-pyridinecarbaldehyde (34160-40-2) + (S)-2-cyano-N-(1-phenylbutyl)acetamide (1240038-58-7) → WP 1130 (856243-80-6)

Guidance literature:

With piperidine; In ethanol; for 3h; Reflux;

DOI:10.1039/c9cc09204h

Reference yield:

(S)-1-amino-1-phenylbutane (3789-60-4) → WP 1130 (856243-80-6)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 2 h / Reflux

2: piperidine / ethanol / 3 h / Reflux

With piperidine; In ethanol; toluene;

DOI:10.1039/c9cc09204h

Reference yield: 82.0%

WP 1130 (856243-80-6) + rac-3-sulfanylpropane-1,2-diol (96-27-5) → 3-(6-Bromopyridin-2-yl)-2-cyano-3-((2,3-dihydroxypropyl)thio)-N-((S)-1-phenylbutyl)propanamide (1369506-58-0)

Guidance literature:

In acetonitrile; at 20 ℃; for 17h;

upstream raw materials:

6-bromo-2-pyridinecarbaldehyde

(S)-2-cyano-N-(1-phenylbutyl)acetamide

(S)-1-amino-1-phenylbutane

Downstream raw materials:

3-(6-Bromopyridin-2-yl)-2-cyano-3-((2,3-dihydroxypropyl)thio)-N-((S)-1-phenylbutyl)propanamide

Refernces

• 1、 -. "COMPOSITIONS AND METHODS OF DELIVERY OF DEUBIQUITINASE INHIBITORS". Paragraph 00348. . Retrieved 2015/12/17.