4-[(3-Bromophenyl)amino]-6-acrylamidoquinazoline

Base Information

• Chemical Name: 4-[(3-Bromophenyl)amino]-6-acrylamidoquinazoline
• CAS No.: 194423-15-9
• Molecular Formula: C17H13BrN4O
• Molecular Weight: 369.22
• UNII: 3R996Y9T0I
• DSSTox Substance ID: DTXSID80274444
• Nikkaji Number: J1.035.909K
• Wikidata: Q26998221
• NCI Thesaurus Code: C2727
• Pharos Ligand ID: TMZ6ZV315MWY
• Metabolomics Workbench ID: 150829
• ChEMBL ID: CHEMBL285063
• Mol file: 194423-15-9.mol

Synonyms:PD168393

Chemical Property of 4-[(3-Bromophenyl)amino]-6-acrylamidoquinazoline

Chemical Property:

• Melting Point: 279℃
• PSA: 70.40000
• LogP: 4.98290
• Storage Temp.: -20°C
• Solubility.: insoluble in H2O; ≥1 mg/mL in EtOH with gentle warming and ultrasonic; ≥18.45 mg/mL in DMSO
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 368.02727
• Heavy Atom Count: 23
• Complexity: 433

Purity/Quality:

98%,99%, ^*data from raw suppliers

PD168393 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C=CC(=O)NC1=CC2=C(C=C1)N=CN=C2NC3=CC(=CC=C3)Br
• Uses: PD 168393, is an irreversible epidermal growth factor receptor (EGFR) inhibitor. PD168393 has been used in the acute inhibition of ErbB4.

Technology Process of 4-[(3-Bromophenyl)amino]-6-acrylamidoquinazoline

There total 11 articles about 4-[(3-Bromophenyl)amino]-6-acrylamidoquinazoline 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: 83.4%

4-(3-bromophenylamino)-6-(3-methoxypropionylamide)-quinazoline (256409-20-8) → PD 168393 (194423-15-9)

Guidance literature:

With potassium tert-butylate; In DMF (N,N-dimethyl-formamide); at 20 ℃; for 5h; Product distribution / selectivity;

Reference yield: 74.3%

4-(3-bromophenylamine)-6-(3-methylsulfonopropionylamide)-quinazoline → PD 168393 (194423-15-9)

Guidance literature:

With potassium tert-butylate; In DMF (N,N-dimethyl-formamide); at 20 - 24 ℃; for 2h; Product distribution / selectivity;

Reference yield: 55.0%

4-(3-bromophenylamine)-6-(3-methylsulfoxidopropionylamide)-quinazoline (256409-24-2) → PD 168393 (194423-15-9)

Guidance literature:

With potassium tert-butylate; In N,N-dimethyl-formamide; at 20 ℃; for 1h; Product distribution / selectivity;

upstream raw materials:

acrylic acid

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

acryloyl chloride

5-nitroanthranilonitrile

Downstream raw materials:

N⁴-(3-bromophenyl)-N⁶-[3-(4-morpholinyl)propyl]-4,6-quinazolinediamine

N-[4-[(3-bromophenyl)-amino]-quinazolin-6-yl]-3-morpholino-propylamide

Refernces

• 1、 -. "QUINAZOLINE AND QUINOLINE DERIVATIVES AS IRREVERSIBLE PROTEIN TYROSINE KINASE INHIBITORS". Page/Page column 27. . Retrieved 2009/05/29.
• 2、 Michalczyk, Anja,Klueter, Sabine,Rode, Haridas B.,Simard, Jeffrey R.,Gruetter, Christian,Rabiller, Matthias,Rauh, Daniel. "Structural insights into how irreversible inhibitors can overcome drug resistance in EGFR". . p. 3482 - 3488. Retrieved 2008/12/21.