7-Hydroxygranisetron

Base Information

• Chemical Name: 7-Hydroxygranisetron
• CAS No.: 133841-15-3
• Molecular Formula: C₁₈H₂₄N₄O₂
• Molecular Weight: 328.414
• Mol file: 133841-15-3.mol

Synonyms:7-Hydroxy-1-methyl-N-[(3-endo)-9-methyl-9-azabicyclo[3.3.1]non-3-yl]-1H-indazole-3-carboxamide

Chemical Property of 7-Hydroxygranisetron

Chemical Property:

• Melting Point: 225-230 °C (decomp)
• Boiling Point: 583.7±50.0 °C(Predicted)
• PKA: 8.90±0.40(Predicted)
• PSA: 70.39000
• Density: 1.41
• LogP: 2.35280

Purity/Quality:

99% ^*data from raw suppliers

7-HydroxyGranisetronLabeledd3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 7-Hydroxygranisetron

There total 5 articles about 7-Hydroxygranisetron 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: 86.0%

7-methoxy-1-methyl-N-[(3-endo)-9-methyl-9-azabicyclo[3.3.1]non-3-yl]-1H-indazole-3-carboxamide (1210745-51-9) → 7-Hydroxy-Granisetron (133841-15-3)

Guidance literature:

7-methoxy-1-methyl-N-[(3-endo)-9-methyl-9-azabicyclo[3.3.1]non-3-yl]-1H-indazole-3-carboxamide; In dichloromethane; at 20 ℃; Ionic liquid; Inert atmosphere; Reflux;

With water; sodium hydroxide; In dichloromethane;

DOI:10.1021/jm901827x

Reference yield:

ethyl 7-methoxy-1H-indazole-3-carboxylate (885278-98-8) → 7-Hydroxy-Granisetron (133841-15-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: methanol; sodium hydroxide / 20 °C / Inert atmosphere

2.1: benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane; N,N-dimethyl-formamide / 20 °C / Inert atmosphere

3.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 0 °C / Inert atmosphere

3.2: 0 - 20 °C / Inert atmosphere

4.1: boron tribromide / dichloromethane / 20 °C / Inert atmosphere

With methanol; potassium tert-butylate; boron tribromide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; sodium hydroxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2011.11.097

Reference yield:

C9H8N2O3 (133841-08-4) → 7-Hydroxy-Granisetron (133841-15-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane; N,N-dimethyl-formamide / 20 °C / Inert atmosphere

2.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 0 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

3.1: boron tribromide / dichloromethane / 20 °C / Inert atmosphere

With potassium tert-butylate; boron tribromide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2011.11.097

upstream raw materials:

7-methoxy-1-methyl-N-[(3-endo)-9-methyl-9-azabicyclo[3.3.1]non-3-yl]-1H-indazole-3-carboxamide

ethyl 7-methoxy-1H-indazole-3-carboxylate

C₉H₈N₂O₃

C₁₈H₂₄N₄O₂

Refernces

• 1、 Vernekar, Sanjeev Kumar V.,Hallaq, Hasan Y.,Clarkson, Guy,Thompson, Andrew J.,Silvestr, Linda,Lummis, Sarah C. R.,Lochner, Martin. "Toward biophysical probes for the 5-HT3 receptor: Structure-activity relationship study of granisetron derivatives". supporting information; experimental part. p. 2324 - 2328. Retrieved 2010/07/17.