(4S)-6-Chloro-4-((E)-2-cyclopropylvinyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one

Base Information

• Chemical Name: (4S)-6-Chloro-4-((E)-2-cyclopropylvinyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one
• CAS No.: 214287-99-7
• Molecular Formula: C₁₄H₁₂ClF₃N₂O
• Molecular Weight: 316.71
• UNII: 2498M8N65F
• Nikkaji Number: J1.282.390H,J2.033.228J
• Wikidata: Q27253830
• ChEMBL ID: CHEMBL29274
• Mol file: 214287-99-7.mol

Synonyms:DPC 083;DPC083

Chemical Property of (4S)-6-Chloro-4-((E)-2-cyclopropylvinyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one

Chemical Property:

• Vapor Pressure: 2.69E-05mmHg at 25°C
• Boiling Point: 357.7°Cat760mmHg
• Flash Point: 170.1°C
• PSA: 41.13000
• Density: 1.544g/cm³
• LogP: 4.66570
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 316.0590252
• Heavy Atom Count: 21
• Complexity: 464

Purity/Quality:

DPC083 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC1C=CC2(C3=C(C=CC(=C3)Cl)NC(=O)N2)C(F)(F)F
• Isomeric SMILES: C1CC1/C=C/[C@]2(C3=C(C=CC(=C3)Cl)NC(=O)N2)C(F)(F)F
• Uses: DPC 083 is a novel anti-HIV drug used in the treatment of the affliction. Used as a non-nucleoside reverse-transcriptase inhibitor, it helps control the replication of genetic material. It is an analog of efavirenz (E425000).

Technology Process of (4S)-6-Chloro-4-((E)-2-cyclopropylvinyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one

There total 14 articles about (4S)-6-Chloro-4-((E)-2-cyclopropylvinyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one 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: 91.0%

(4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1,3,4-trihydroquinazolin-2-one (214287-88-4) → (S,E)-6-chloro-4-(2-cyclopropylvinyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one (214287-99-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; 1,2-dichloro-benzene; at -78 - 20 ℃;

DOI:10.1021/jm990580e

Reference yield: 62.0%

C22H20ClF3N2O2 → (S,E)-6-chloro-4-(2-cyclopropylvinyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one (214287-99-7)

Guidance literature:

With trifluoroacetic acid; at 70 ℃; for 0.5h;

DOI:10.1002/chem.201303307

Reference yield: 60.0%

(S,E)-6-chloro-4-(2-cyclopropylvinyl)-1-(4-methoxybenzyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one (1360591-23-6) → (S,E)-6-chloro-4-(2-cyclopropylvinyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one (214287-99-7)

Guidance literature:

With trifluoroacetic acid; at 70 ℃; for 0.5h;

DOI:10.1039/c2cc36307k DOI:10.1039/c2cc36307k

upstream raw materials:

(4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1,3,4-trihydroquinazolin-2-one

(4S)-6-chloro-4-(2-cyclopropyl-2-hydroxyethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one

(R)-6-chloro-1-(4-methoxybenzyl)-2-oxo-4-(trifluoromethyl)-1,2,3,4-tetrahydroquinazoline-4-carbonitrile

C₁₈H₁₄ClF₃N₂O₃