Efavirenz impurity I

Base Information

• Chemical Name: Efavirenz impurity I
• CAS No.: 209414-26-6
• Molecular Formula: C₂₁H₁₇ClF₃NO₂
• Molecular Weight: 407.82
• UNII: S40TCL042S
• Nikkaji Number: J1.518.905C
• Wikidata: Q27288554
• Mol file: 209414-26-6.mol

Synonyms:Efavirenz impurity I;209414-26-6;SG-275;S40TCL042S;UNII-S40TCL042S;(2RS,4S)-6-Chloro-4-(2-cyclopropyleth-1-yn-1-yl)-2-(4-methoxyphenyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazine;(4S)-6-chloro-4-(2-cyclopropylethynyl)-2-(4-methoxyphenyl)-4-(trifluoromethyl)-1,2-dihydro-3,1-benzoxazine;(4S)-6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-2-(4-methoxyphenyl)-4-(trifluoromethyl)-2H-3,1-benz;(4S)-6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-2-(4-methoxyphenyl)-4-(trifluoromethyl)-2H-3,1-benzoxazine;SCHEMBL6730698;UTEUZELNJWOZOI-ANYOKISRSA-N;(4S)-6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-2-(4-methoxyphenyl)-4-(trifluoromethyl)-2H-3,1-benzoxazine_x000b_(Mixture of 2 Diastereomers);J-013731;Q27288554;(4S)-6-chloro-4-(2-cyclopropylethynyl)-2-(4-methoxyphenyl)-4-(trifluoromethyl)-1, 2-dihydro-3, 1-benzoxazine

Chemical Property of Efavirenz impurity I

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 97-100°C
• Boiling Point: 515.1±50.0 °C(Predicted)
• PKA: -0.71±0.60(Predicted)
• Density: 1.40±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility.: Methanol (Slightly)
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 407.0899910
• Heavy Atom Count: 28
• Complexity: 633

Purity/Quality:

95% ^*data from raw suppliers

(4S)-6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-2-(4-methoxyphenyl)-4-(trifluoromethyl)-2H-3,1-benzoxazine(Mixtureof2Diastereomers) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C2NC3=C(C=C(C=C3)Cl)C(O2)(C#CC4CC4)C(F)(F)F
• Isomeric SMILES: COC1=CC=C(C=C1)C2NC3=C(C=C(C=C3)Cl)[C@@](O2)(C#CC4CC4)C(F)(F)F
• Uses: An impurity arising in the synthesis of Efavirenz (E425000).

Technology Process of Efavirenz impurity I

There total 9 articles about Efavirenz impurity I 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:

4-Methoxybenzyl alcohol (105-13-5) → 6-chloro-4-cyclopropylethynyl-2-(4-methoxy-phenyl)-4-trifluoromethyl-1,4-dihydro-2H-benzo[d][1,3]oxazine (209414-26-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / p-toluenesulfonic acid monohydrate / acetonitrile / 2 h / Heating

2: 1.) (1R,2S)-N-pyrrolidinylnorephedrine lithium alkoxide, triphenylmethane / 1.) THF, toluene, hexanes, 0-5 deg C, 30 min, 2.) THF, toluene, hexanes, -55 deg C, 60 min

3: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / toluene / 2 h / Ambient temperature; other reagent: chloranil

With triphenylmethane; (1R,2S)-N-pyrrolidinylnorephedrine lithium alkoxide; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In toluene; acetonitrile;

DOI:10.1021/jo981170l

Reference yield:

4-Methoxybenzyl alcohol (105-13-5) → 6-chloro-4-cyclopropylethynyl-2-(4-methoxy-phenyl)-4-trifluoromethyl-1,4-dihydro-2H-benzo[d][1,3]oxazine (209414-26-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / p-toluenesulfonic acid monohydrate / acetonitrile / 2 h / Heating

2: 1.) (1R,2S)-N-pyrrolidinylnorephedrine lithium alkoxide, triphenylmethane / 1.) THF, toluene, hexanes, 0-5 deg C, 30 min, 2.) THF, toluene, hexanes, -55 deg C, 60 min

3: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / toluene / 2 h / Ambient temperature; other reagent: chloranil

With triphenylmethane; (1R,2S)-N-pyrrolidinylnorephedrine lithium alkoxide; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In toluene; acetonitrile;

DOI:10.1021/jo981170l

Reference yield:

1-{5-chloro-2-[(4-methoxybenzyl)amino]phenyl}-2,2,2-trifluoroethan-1-one (173676-54-5) → 6-chloro-4-cyclopropylethynyl-2-(4-methoxy-phenyl)-4-trifluoromethyl-1,4-dihydro-2H-benzo[d][1,3]oxazine (209414-26-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) (1R,2S)-N-pyrrolidinylnorephedrine lithium alkoxide, triphenylmethane / 1.) THF, toluene, hexanes, 0-5 deg C, 30 min, 2.) THF, toluene, hexanes, -55 deg C, 60 min

2: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / toluene / 2 h / Ambient temperature; other reagent: chloranil

With triphenylmethane; (1R,2S)-N-pyrrolidinylnorephedrine lithium alkoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In toluene;

DOI:10.1021/jo981170l

upstream raw materials:

(S)-5-chloro-α-(cyclopropylethynyl)-2-<<(4-methoxyphenyl)methyl>amino>-α-(trifluoromethyl)benzenemethanol

4-Methoxybenzyl alcohol

1-(2-amino-5-chloro-phenyl)-2,2,2-trifluoro-ethanone

1-{5-chloro-2-[(4-methoxybenzyl)amino]phenyl}-2,2,2-trifluoroethan-1-one

Downstream raw materials:

6-chloro-2-cyclopropyl-4-(trifluoromethyl)quinoline