214287-90-8

Basic information

• Product Name: 4(S)-(2-Cyclopropylethynyl)-5,6-difluoro-4-(trifluoromethyl)-3,4-dihydro-1H-quinazolin-2-one
• Synonyms: DPC-963; DMP-963; (4S)-4-(cyclopropylethynyl)-5,6-difluoro-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one
• CAS NO: 214287-90-8
• Molecular Formula: C₁₄H₉F₅N₂O
• Molecular Weight: 316.2261
• Mol File: 214287-90-8.mol

Chemical Properties

• Boiling Point: 340.3°C at 760 mmHg
• Flash Point: 159.6°C
• Density: 1.54g/cm³
• Vapor Pressure: 8.67E-05mmHg at 25°C
• Refractive Index: 1.554
• CAS DataBase Reference: 4(S)-(2-Cyclopropylethynyl)-5,6-difluoro-4-(trifluoromethyl)-3,4-dihydro-1H-quinazolin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4(S)-(2-Cyclopropylethynyl)-5,6-difluoro-4-(trifluoromethyl)-3,4-dihydro-1H-quinazolin-2-one(214287-90-8)
• EPA Substance Registry System: 4(S)-(2-Cyclopropylethynyl)-5,6-difluoro-4-(trifluoromethyl)-3,4-dihydro-1H-quinazolin-2-one(214287-90-8)

Safety Data

• Hazardous Substances Data: 214287-90-8(Hazardous Substances Data)

Upstream product

• 6746-94-7 Cyclopropylacetylene 
• 214288-05-8 5,6-difluoro-4-trifluoromethylquinazolin-2(1H)-one 
• 201218-09-9 cyclopropyl acetylenyllithium 
• 205756-47-4 o-aminotrifluoromethyl ketone 
• 214288-04-7 5,6-difluoro-3,4-dihydro-4-hydroxy-4-trifluoromethylquinazolin-2(1H)-one 

Relevant articles and documents

NMR spectroscopic investigations of mixed aggregates underlying highly enantioselective 1,2-additions of lithium cyclopropylacetylide to quinazolinones

The solution structures of mixed aggregates derived from lithium alkoxides and lithium acetylides were investigated as part of a program to develop practical syntheses of quinazolinone-based nonnucleoside reverse transcriptase inhibitors. Low-temperature 6Li, 13C, and 15N NMR spectroscopies reveal that mixtures of lithium cyclopropylacetylide (RCCLi), a (+)-carene-derived amino alkoxide (R*OLi), and lithium hexamethyldisilazide (LiHMDS) in THF/pentane afford a (RCCLi)3(R*OLi) mixed tetramer, a C2-symmetric and asymmetric (RCCLi)2(R*OLi)2 mixed tetramer, and a C3-symmetric (RCCLi)(R*OLi)3 mixed tetramer. Analogous mixtures of RCCLi/R*OLi in Et2O and Me2NEt also provide 3:1, 2:2, and 1:3 mixed tetramers. The stereochemistry of aggregation is highly sensitive to the medium. The C2-symmetric (RCCLi)2(R*OLi)2 mixed tetramer is formed in Et2O, whereas the asymmetric isomer is formed in Me2NEt. LiHMDS in THF is shown to be an efficient proton scavenger without forming LiHMDS-RCCLi or LiHMDS-R*OLi mixed aggregates. LiHMDS-RCCLi mixtures form mixed aggregates in Me2NEt.

An efficient chiral moderator prepared from inexpensive (+)-3-Carene: Synthesis of the HIV-1 non-nucleoside reverse transcriptase inhibitor DPC 963

(matrix presented) The β-amino alcohol 4β-morpholinocaran-3α-ol is prepared by addition of morpholine to α-3,4-epoxycarane utilizing anhydrous magnesium bromide as Lewis acid promoter. The enantiopure amino alcohol is uniquely effective as a chiral moderator for the addition of lithium cyclopropylacetylide to an unprotected N-acylketimine. This reaction provides an efficient route to the second generation NNRTI drug candidate DPC 963.

Asymmetric synthesis of quinazolin-2-ones useful as HIV reverse transcriptase inhibitors

This invention relates generally to the asymmetric synthesis of quinazolin-2-ones that are useful as inhibitors of HIV reverse transcriptase. The synthesis is accomplished through the chiral ligand mediated addition of cyclopropylacetylide.

Asymmetric synthesis of quinazolin-2-ones useful as HIV reverse transcriptase inhibitors

This invention relates generally to the asymmetric synthesis of quinazolin-2-ones that are useful as inhibitors of HIV reverse transcriptase. The synthesis is accomplished through the chiral ligand mediated addition of cyclopropylacetylide.