3-Bromo Nevirapine

Base Information

• Chemical Name: 3-Bromo Nevirapine
• CAS No.: 284686-21-1
• Molecular Formula: C₁₅H₁₃BrN₄O
• Molecular Weight: 345.198
• DSSTox Substance ID: DTXSID80443572
• Wikidata: Q82261460
• Mol file: 284686-21-1.mol

Synonyms:3-Bromo Nevirapine;284686-21-1;6-bromo-2-cyclopropyl-7-methyl-2,4,9,15-tetrazatricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,12,14-hexaen-10-one;DTXSID80443572;CS-T-49833;3-Bromo-11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one;FT-0663809;J-017103

Chemical Property of 3-Bromo Nevirapine

Chemical Property:

• Boiling Point: 450.3±45.0 °C(Predicted)
• PKA: 11.35±0.20(Predicted)
• PSA: 61.61000
• Density: 1.619±0.06 g/cm3(Predicted)
• LogP: 3.29830
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly, Sonicated), Dichloromethane (Slightly), Ethyl Acetate (Sli
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 344.02727
• Heavy Atom Count: 21
• Complexity: 430

Purity/Quality:

97% ^*data from raw suppliers

3-Bromo Nevirapine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C(=NC=C1Br)N(C3=C(C=CC=N3)C(=O)N2)C4CC4
• Uses: Intermediate in the preparation of Nevirapine metabolites.

Technology Process of 3-Bromo Nevirapine

There total 7 articles about 3-Bromo 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: 92.7%

2-chloro-N-[5'-bromo-4'-methyl-2'-cyclopropylamino-3'-pyridinyl]-3-pyridinecarboxamide (284686-20-0) → 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)

Guidance literature:

With pyridine; sodium hydride; for 0.5h; Heating;

DOI:10.1002/jhet.5570370203

Reference yield:

2-chloro-3-nitro-4-methylpyridine (23056-39-5) → 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)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; hydrogen; bromine; potassium acetate; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; nickel; In ethanol; ethyl acetate; xylene; 1: Substitution / 2: Reduction / 3: Condensation / 4: Bromination / 5: Cyclization;

DOI:10.1002/jhet.5570370203

Reference yield:

2-(cyclopropylamino)-4-methyl-3-nitropyridine (284686-17-5) → 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)

Guidance literature:

Multi-step reaction with 4 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

With pyridine; hydrogen; bromine; potassium acetate; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; nickel; In ethanol; ethyl acetate; 1: Reduction / 2: Condensation / 3: Bromination / 4: Cyclization;

DOI:10.1002/jhet.5570370203

upstream raw materials:

2-chloro-N-[5'-bromo-4'-methyl-2'-cyclopropylamino-3'-pyridinyl]-3-pyridinecarboxamide

2-Chloronicotinoyl chloride

2-chloronicotinic acid

2-chloro-3-nitro-4-methylpyridine

Downstream raw materials:

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

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