N-[5-Bromo-2-(cyclopropylamino)-4-methyl-3-pyridinyl]-2-chloro-3-pyridinecarboxamide

Base Information

• Chemical Name: N-[5-Bromo-2-(cyclopropylamino)-4-methyl-3-pyridinyl]-2-chloro-3-pyridinecarboxamide
• CAS No.: 284686-20-0
• Molecular Formula: C₁₅H₁₄BrClN₄O
• Molecular Weight: 381.659
• DSSTox Substance ID: DTXSID20442923
• Wikidata: Q82260529
• Mol file: 284686-20-0.mol

Synonyms:284686-20-0;N-[5-Bromo-2-(cyclopropylamino)-4-methyl-3-pyridinyl]-2-chloro-3-pyridinecarboxamide;N-[5-bromo-2-(cyclopropylamino)-4-methylpyridin-3-yl]-2-chloropyridine-3-carboxamide;AGN-PC-0N831S;DTXSID20442923;GMTLDWLAZXKJQE-UHFFFAOYSA-N;FT-0663684;J-017102

Chemical Property of N-[5-Bromo-2-(cyclopropylamino)-4-methyl-3-pyridinyl]-2-chloro-3-pyridinecarboxamide

Chemical Property:

• PSA: 70.40000
• LogP: 4.48450
• Solubility.: Dichloromethane
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 380.00395
• Heavy Atom Count: 22
• Complexity: 409

Purity/Quality:

97% ^*data from raw suppliers

N-[5-Bromo-2-(cyclopropylamino)-4-methyl-3-pyridinyl]-2-chloro-3-pyridinecarboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C(=NC=C1Br)NC2CC2)NC(=O)C3=C(N=CC=C3)Cl
• Uses: Intermediate in the preparation of Nevirapine metabolites.

Technology Process of N-[5-Bromo-2-(cyclopropylamino)-4-methyl-3-pyridinyl]-2-chloro-3-pyridinecarboxamide

There total 6 articles about N-[5-Bromo-2-(cyclopropylamino)-4-methyl-3-pyridinyl]-2-chloro-3-pyridinecarboxamide 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: 30.0%

2-chloro-N-[(2'-cyclopropylamino)-4'-methyl-3'-pyridyl]-3-pyridinecarboxamide (284686-19-7) → 2-chloro-N-[5'-bromo-4'-methyl-2'-cyclopropylamino-3'-pyridinyl]-3-pyridinecarboxamide (284686-20-0)

Guidance literature:

With bromine; potassium acetate; acetic acid; at 20 ℃; for 1h;

DOI:10.1002/jhet.5570370203

Reference yield:

2-chloro-3-nitro-4-methylpyridine (23056-39-5) → 2-chloro-N-[5'-bromo-4'-methyl-2'-cyclopropylamino-3'-pyridinyl]-3-pyridinecarboxamide (284686-20-0)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1002/jhet.5570370203

Reference yield:

2-(cyclopropylamino)-4-methyl-3-nitropyridine (284686-17-5) → 2-chloro-N-[5'-bromo-4'-methyl-2'-cyclopropylamino-3'-pyridinyl]-3-pyridinecarboxamide (284686-20-0)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1002/jhet.5570370203

upstream raw materials:

2-chloro-N-[(2'-cyclopropylamino)-4'-methyl-3'-pyridyl]-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

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