5-bromo-N-methoxy-N-methylnicotinamide

Base Information

• Chemical Name: 5-bromo-N-methoxy-N-methylnicotinamide
• CAS No.: 183608-47-1
• Molecular Formula: C8H9BrN2O2
• Molecular Weight: 245.076
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID40594195
• Nikkaji Number: J1.409.524A
• Wikidata: Q82488966
• Mol file: 183608-47-1.mol

Synonyms:5-bromo-N-methoxy-N-methylnicotinamide;183608-47-1;5-bromo-N-methoxy-N-methylpyridine-3-carboxamide;3-Pyridinecarboxamide, 5-bromo-N-methoxy-N-methyl-;MFCD07370042;N-methyl-N-methoxy-5-bromopyridine-3-carboxamide;SCHEMBL480826;DTXSID40594195;YWTGVFDGOFXIPM-UHFFFAOYSA-N;AKOS005071545;AB32489;AD-0735;5-Bromo-N-methoxy-N-methyl-nicotinamide;AM803405;DB-368620;CS-0195758;A880816;J-517189;F1903-0092

Chemical Property of 5-bromo-N-methoxy-N-methylnicotinamide

Chemical Property:

• Boiling Point: 367.3±27.0 °C(Predicted)
• PKA: 0.80±0.20(Predicted)
• PSA: 42.43000
• Density: 1.526±0.06 g/cm3(Predicted)
• LogP: 1.47750
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 243.98474
• Heavy Atom Count: 13
• Complexity: 189

Purity/Quality:

97% ^*data from raw suppliers

5-Bromo-N-methoxy-N-methylnicotinamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C(=O)C1=CC(=CN=C1)Br)OC
• Uses: 5-Bromo-N-methoxy-N-methylnicotinamide is a useful reagent used in the preparation and in the discovery of potent, selective and peripherally restricted pan-Trk inhibitor (PF-06273340) for the treatment of pain.

Technology Process of 5-bromo-N-methoxy-N-methylnicotinamide

There total 4 articles about 5-bromo-N-methoxy-N-methylnicotinamide 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: 97.0%

5-bromo-3-pyridinecarboxylic acid (20826-04-4) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → N-methyl-N-methoxy-5-bromopyridine-3-carboxamide (183608-47-1)

Guidance literature:

5-bromo-3-pyridinecarboxylic acid; With 1,1'-carbonyldiimidazole; In dichloromethane; at 15 - 25 ℃;

N,O-dimethylhydroxylamine*hydrochloride; With triethylamine; In dichloromethane; at 5 - 25 ℃;

Reference yield: 88.0%

5-bromonicotinoyl chloride (39620-02-5) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → N-methyl-N-methoxy-5-bromopyridine-3-carboxamide (183608-47-1)

Guidance literature:

With triethylamine; In chloroform; at 0 - 20 ℃; for 1.58333h;

DOI:10.1021/jm050670l

Reference yield: 85.0%

5-bromo-3-pyridinecarboxylic acid (20826-04-4) + N,0-dimethylhydroxylamine (1117-97-1) → N-methyl-N-methoxy-5-bromopyridine-3-carboxamide (183608-47-1)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

upstream raw materials:

5-bromonicotinoyl chloride

N,O-dimethylhydroxylamine*hydrochloride

5-bromo-3-pyridinecarboxylic acid

N,0-dimethylhydroxylamine

Downstream raw materials:

5-bromopyridine-3-carbaldehyde

(5-bromo-3-pyridinyl)(5-chloro-2-hydroxyphenyl)methanone

5-[(5-chloro-2-hydroxyphenyl)carbonyl]-3-pyridinecarbonitrile

(5-bromopyridin-3-yl)(phenyl)methanone