2-methyl-N-(9-methyl-9-azabicyclo[3.3.1]nonan-3-yl)indazole-3-carboxamide

Base Information

• Chemical Name: 2-methyl-N-(9-methyl-9-azabicyclo[3.3.1]nonan-3-yl)indazole-3-carboxamide
• CAS No.: 127472-42-8
• Molecular Formula: C18H24N4O
• Molecular Weight: 312.415
• Hs Code.: 2933399090
• ChEMBL ID: CHEMBL301877
• DSSTox Substance ID: DTXSID20564038
• Mol file: 127472-42-8.mol

Synonyms:127472-42-8;1-Desmethyl 2-Methyl Granisetron (Granisetron Impurity A);2-methyl-N-(9-methyl-9-azabicyclo[3.3.1]nonan-3-yl)indazole-3-carboxamide;2H-Indazole-3-carboxamide, 2-methyl-N-[(3-endo)-9-methyl-9-azabicyclo[3.3.1]non-3-yl]-;Granisetron Impurity A;2-Methyl-N-(9-methyl-9-azabicyclo[3.3.1]nonan-3-yl)-2H-indazole-3-carboxamide;1-Desmethyl 2-Methyl Granisetron;2-methyl-N-{9-methyl-9-azabicyclo[3.3.1]nonan-3-yl}-2H-indazole-3-carboxamide;CHEMBL301877;DTXSID20564038;BCP16094;AKOS027460975;BS-42114;J-005495;2-Methyl-2H-indazole-3-carboxylic acid (9-methyl-9-aza-bicyclo[3.3.1]non-3-yl)-amide;endo-N-(9-Methyl-9-Azabicyclo[3.3.1]non-3-yl)-2-methyl-2H-indazole -3-carboxamide

Chemical Property of 2-methyl-N-(9-methyl-9-azabicyclo[3.3.1]nonan-3-yl)indazole-3-carboxamide

Chemical Property:

• Melting Point: 245-248
• Boiling Point: 552.3±40.0 °C(Predicted)
• PKA: 13.26±0.20(Predicted)
• PSA: 50.16000
• Density: 1.33±0.1 g/cm3(Predicted)
• LogP: 2.64720
• Storage Temp.: -20°C Freezer
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 312.19501140
• Heavy Atom Count: 23
• Complexity: 442

Purity/Quality:

99%, ^*data from raw suppliers

1-Desmethyl2-MethylGranisetron ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2CCCC1CC(C2)NC(=O)C3=C4C=CC=CC4=NN3C
• Uses: An impurity in the synthesis of Granisetron Hydrochloride. Granisetron Impurity A.

Technology Process of 2-methyl-N-(9-methyl-9-azabicyclo[3.3.1]nonan-3-yl)indazole-3-carboxamide

There total 2 articles about 2-methyl-N-(9-methyl-9-azabicyclo[3.3.1]nonan-3-yl)indazole-3-carboxamide 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:

2-Methylindazole-3-carboxylic acid (34252-44-3) → endo-N-(9-methyl-9-azabicyclo<3.3.1>nonan-3-yl)-2-methyl-2H-indazole-3-carboxamide (127472-42-8)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride, DMF / CH₂Cl₂ / 1 h

2: Et₃N / CH₂Cl₂ / 2 h

With oxalyl dichloride; triethylamine; N,N-dimethyl-formamide; In dichloromethane;

DOI:10.1021/jm00169a016

Reference yield:

endo-9-methyl-9-azabicyclo[3.3.1]nonan-3-amine (76272-41-8,141650-55-7,76272-56-5) + 2-methyl-2H-indazole-3-carbonyl chloride (181071-92-1) → endo-N-(9-methyl-9-azabicyclo<3.3.1>nonan-3-yl)-2-methyl-2H-indazole-3-carboxamide (127472-42-8)

Guidance literature:

With triethylamine; In dichloromethane; for 2h; Yield given;

DOI:10.1021/jm00169a016

upstream raw materials:

endo-9-methyl-9-azabicyclo[3.3.1]nonan-3-amine

2-methyl-2H-indazole-3-carbonyl chloride

2-Methylindazole-3-carboxylic acid