N-(4-((3-bromophenyl)amino)quinazolin-6-yl)but-2-ynamide

Base Information

• Chemical Name: N-(4-((3-bromophenyl)amino)quinazolin-6-yl)but-2-ynamide
• CAS No.: 194423-06-8
• Molecular Formula: C18H13BrN4O
• Molecular Weight: 381.231
• UNII: B4W27J1Z8B
• DSSTox Substance ID: DTXSID401236539
• Nikkaji Number: J1.079.050F
• Wikidata: Q27162381
• Pharos Ligand ID: 9CU61QQVS9LU
• ChEMBL ID: CHEMBL91867
• Mol file: 194423-06-8.mol

Synonyms:CL 387785;CL-387,785;CL-387785;EKI 785;EKI-785;N-(4-((3-bromophenyl)amino)-6-quinazolinyl)-2-butynamide

Chemical Property of N-(4-((3-bromophenyl)amino)quinazolin-6-yl)but-2-ynamide

Chemical Property:

• Melting Point: 276 °C
• PKA: 9.84±0.43(Predicted)
• PSA: 70.40000
• Density: 1.577±0.06 g/cm3(Predicted)
• LogP: 4.82020
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility.: insoluble in EtOH; insoluble in H2O; ≥16.85 mg/mL in DMSO
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 380.02727
• Heavy Atom Count: 24
• Complexity: 514

Purity/Quality:

99% ^*data from raw suppliers

CL-387785(EKI-785) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC#CC(=O)NC1=CC2=C(C=C1)N=CN=C2NC3=CC(=CC=C3)Br
• Description: Overactivity of epidermal growth factor receptor (EGFR) tyrosine kinase activity has been associated with a number of cancers. CL 387,785 is a potent, irreversible inhibitor of EGFR kinase activity (IC50 = 370 pM). It blocks EGF-stimulated autophosphorylation of receptors in cells (IC50 = 5 nM) and halts cell cycling in cells that overexpress EGFR or c-ErbB2 (IC50s = 31-125 nM). CL 387,785 profoundly blocks the growth of EGFR-overexpressing tumors in nude mice when given orally at 80 mg/kg/day for 10 days.
• Uses: CL-387785 (EKI-785) is an irreversible and selective EGFR inhibitor showing activity against mutations of the receptor. Potential therapeutic against various type of cancer, including lung cancer.

Technology Process of N-(4-((3-bromophenyl)amino)quinazolin-6-yl)but-2-ynamide

There total 13 articles about N-(4-((3-bromophenyl)amino)quinazolin-6-yl)but-2-ynamide 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: 5.0%

2-Butynoic acid (590-93-2) + 6-amino-4-[(3-bromophenyl)amino]quinazoline (169205-78-1) → N-[4-[(3-bromophenyl)amino]-6-quinazolinyl]-2-butynamide (194423-06-8)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 25 ℃; for 48h;

DOI:10.1021/jm050936o

Reference yield:

[4-chloro-6-quinazolinyl]-2-butynamide + m-Bromoaniline (591-19-5) → N-[4-[(3-bromophenyl)amino]-6-quinazolinyl]-2-butynamide (194423-06-8)

Guidance literature:

In isopropyl alcohol;

Reference yield:

N-[3-cyano-4-[[(dimethylamino)methylene]amino]phenyl]-2-butynamide + m-Bromoaniline (591-19-5) → N-[4-[(3-bromophenyl)amino]-6-quinazolinyl]-2-butynamide (194423-06-8)

Guidance literature:

In acetic acid;

upstream raw materials:

6-amino-4-[(3-bromophenyl)amino]quinazoline

2-Butynoic acid

5-nitroanthranilonitrile

6-nitro-4-(3-bromophenylaniline)quinazoline

Refernces

• 1、 -. "SUBSTITUTED QUINAZOLINE DERIVATIVES AND THEIR USE AS TYROSINE KINASE INHIBITORS". Page 34. . Retrieved 2010/02/07.
• 2、 -. "Irreversible inhibitors of tyrosine kinases". Page column 64. . Retrieved 2008/06/13.