3-Ethenyl Nevirapine

Base Information

• Chemical Name: 3-Ethenyl Nevirapine
• CAS No.: 284686-22-2
• Molecular Formula: C₁₇H₁₆N₄O
• Molecular Weight: 292.34
• DSSTox Substance ID: DTXSID40445178
• Wikidata: Q82263528
• Mol file: 284686-22-2.mol

Synonyms:3-Ethenyl Nevirapine;284686-22-2;2-cyclopropyl-6-ethenyl-7-methyl-2,4,9,15-tetrazatricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,12,14-hexaen-10-one;2-cyclopropyl-6-ethenyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0?,?]pentadeca-1(11),3,5,7,12,14-hexaen-10-one;DTXSID40445178;FT-0667987;11-Cyclopropyl-3-ethenyl-5,11-dihydro-4-methyl-6H-dipyrido(3,2-b:2',3'-e)(1,4)diazepin-6-one

Chemical Property of 3-Ethenyl Nevirapine

Chemical Property:

• Boiling Point: 450.6±45.0 °C(Predicted)
• PKA: 11.88±0.20(Predicted)
• PSA: 61.61000
• Density: 1.311±0.06 g/cm3(Predicted)
• LogP: 3.17880
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 292.13241115
• Heavy Atom Count: 22
• Complexity: 464

Purity/Quality:

97% ^*data from raw suppliers

3-Ethenyl Nevirapine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C(=NC=C1C=C)N(C3=C(C=CC=N3)C(=O)N2)C4CC4

Technology Process of 3-Ethenyl Nevirapine

There total 8 articles about 3-Ethenyl Nevirapine 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: 64.9%

tri-n-butyl(vinyl)tin (7486-35-3) + 3-bromo-11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (284686-21-1) → 11-cyclopropyl-5,11-dihydro-4-methyl-3-vinyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (284686-22-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 90 ℃; for 1.5h;

DOI:10.1002/jhet.5570370203

Reference yield:

2-chloro-3-nitro-4-methylpyridine (23056-39-5) → 11-cyclopropyl-5,11-dihydro-4-methyl-3-vinyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (284686-22-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / xylene / 48 h / 75 °C

2: 55 percent / H₂ / Raney Ni / ethanol / 4 h / 2068.59 Torr

3: 71 percent / N,N-diisopropylethylamine / ethyl acetate / 18 h / 20 °C

4: 30 percent / potassium acetate; acetic acid; bromine / 1 h / 20 °C

5: 92.7 percent / sodium hydride; pyridine / 0.5 h / Heating

6: 64.9 percent / tetrakis(triphenylphosphine)palladium / dimethylformamide / 1.5 h / 90 °C

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; bromine; potassium acetate; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; nickel; In ethanol; ethyl acetate; N,N-dimethyl-formamide; xylene; 1: Substitution / 2: Reduction / 3: Condensation / 4: Bromination / 5: Cyclization / 6: Alkylation;

DOI:10.1002/jhet.5570370203

Reference yield:

2-(cyclopropylamino)-4-methyl-3-nitropyridine (284686-17-5) → 11-cyclopropyl-5,11-dihydro-4-methyl-3-vinyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (284686-22-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 55 percent / H₂ / Raney Ni / ethanol / 4 h / 2068.59 Torr

2: 71 percent / N,N-diisopropylethylamine / ethyl acetate / 18 h / 20 °C

3: 30 percent / potassium acetate; acetic acid; bromine / 1 h / 20 °C

4: 92.7 percent / sodium hydride; pyridine / 0.5 h / Heating

5: 64.9 percent / tetrakis(triphenylphosphine)palladium / dimethylformamide / 1.5 h / 90 °C

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; bromine; potassium acetate; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; nickel; In ethanol; ethyl acetate; N,N-dimethyl-formamide; 1: Reduction / 2: Condensation / 3: Bromination / 4: Cyclization / 5: Alkylation;

DOI:10.1002/jhet.5570370203

upstream raw materials:

tri-n-butyl(vinyl)tin

3-bromo-11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

2-Chloronicotinoyl chloride

2-chloronicotinic acid

Downstream raw materials:

11-cyclopropyl-5,11-dihydro-3-formyl-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one