2-(2-Chloroquinazolin-4-yl)acetamide

Base Information

• Chemical Name: 2-(2-Chloroquinazolin-4-yl)acetamide
• CAS No.: 425638-74-0
• Molecular Formula: C10H8ClN3O
• Molecular Weight: 221.64302
• Hs Code.: 2933990090
• European Community (EC) Number: 610-041-1
• DSSTox Substance ID: DTXSID30596143
• Wikidata: Q82491303
• Mol file: 425638-74-0.mol

Synonyms:2-(2-Chloroquinazolin-4-yl)acetamide;425638-74-0;2-(2-CHLOROQUINAZOLINE-4-YL)-ACETAMIDE;DE-0070;SCHEMBL1991028;2-Chloro-4-quinazolineacetamide;DTXSID30596143;HBENSHGDVIJNBK-UHFFFAOYSA-N;AMY10671;MFCD16627975;2-(2-chloro-4-quinazolinyl)acetamide;AKOS015993906;SB17903;2-(2-chloroquinazolin-4-yl) acetamide;2-(2-chloro-quinazolin-4-yl)-acetamide;AC-30715;DB-392965;CS-0005837;W17508;A872858

Chemical Property of 2-(2-Chloroquinazolin-4-yl)acetamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 373.077°C at 760 mmHg
• Flash Point: 179.431°C
• PSA: 69.86000
• Density: 1.425g/cm³
• LogP: 2.46070
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 221.0355896
• Heavy Atom Count: 15
• Complexity: 249

Purity/Quality:

NLT 98% ^*data from raw suppliers

2-(2-chloroquinazolin-4-yl)acetamide 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=NC(=N2)Cl)CC(=O)N

Technology Process of 2-(2-Chloroquinazolin-4-yl)acetamide

There total 4 articles about 2-(2-Chloroquinazolin-4-yl)acetamide 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: 54.0%

2,4-dichloroquinazoline (607-68-1) + ethyl acetoacetate (141-97-9) → 2-(2-chloroquinazolin-4-yl)acetamide (425638-74-0)

Guidance literature:

ethyl acetoacetate; With sodium hydride; In tetrahydrofuran; at 0 ℃;

2,4-dichloroquinazoline; In toluene; at 140 ℃; for 0.5h;

With ammonium hydroxide; In water; at 20 ℃;

DOI:10.1021/jm901108b

Reference yield:

C12H11ClN2O2 → 2-(2-chloroquinazolin-4-yl)acetamide (425638-74-0)

Guidance literature:

With ammonium hydroxide; In ethanol; at 20 - 50 ℃; for 23.5h;

Reference yield:

1,2,3,4-tetrahydro-quinazoline-2,4-dione (86-96-4) → 2-(2-chloroquinazolin-4-yl)acetamide (425638-74-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N,N-dimethyl-aniline; trichlorophosphate / 3 h / 110 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

2.2: 0.5 h / 110 °C / Inert atmosphere

With sodium hydride; N,N-dimethyl-aniline; trichlorophosphate; In tetrahydrofuran; mineral oil;

DOI:10.1021/jm200469u

upstream raw materials:

2,4-dichloroquinazoline

ethyl acetoacetate

1,2,3,4-tetrahydro-quinazoline-2,4-dione

Downstream raw materials:

2-[2-(4-methyl-piperazin-1-yl)-quinazolin-4-yl]-acetamide

sotrastaurin

Refernces

• 1、 Wagner, Jürgen,Von Matt, Peter,Faller, Bernard,Cooke, Nigel G.,Albert, Rainer,Sedrani, Richard,Wiegand, Hansj?rg,Jean, Christian,Beerli, Christian,Weckbecker, Gisbert,Evenou, Jean-Pierre,Zenke, Gerhard,Cottens, Sylvain. "Structure-activity relationship and pharmacokinetic studies of sotrastaurin (aeb071), a promising novel medicine for prevention of graft rejection and treatment of psoriasis". experimental part. p. 6028 - 6039. Retrieved 2011/10/09.
• 2、 Wagner, Jürgen,Von Matt, Peter,Sedrani, Richard,Albert, Rainer,Cooke, Nigel,Ehrhardt, Claus,Geiser, Martin,Rummel, Gabriele,Stark, Wilhelm,Strauss, Andre,Cowan-Jacob, Sandra W.,Beerli, Christian,Weckbecker, Gisbert,Evenou, Jean-Pierre,Zenke, Gerhard,Cottens, Sylvain. "Discovery of 3-(1H-indol-3-yl)-4-[2-(4-methylpiperazin-1-yl)quinazolin-4- yl]-pyrrole-2,5-dione (AEB071), a potent and selective inhibitor of protein kinase C isotypes". supporting information; experimental part. p. 6193 - 6196. Retrieved 2010/04/02.