Des(dimethylamino)hydroxyrizatriptan

Base Information

• Chemical Name: Des(dimethylamino)hydroxyrizatriptan
• CAS No.: 160194-39-8
• Molecular Formula: C13H14 N4 O
• Molecular Weight: 242.28
• European Community (EC) Number: 620-292-9
• UNII: GUF1804OA0
• DSSTox Substance ID: DTXSID20166834
• Nikkaji Number: J984.691C
• Wikidata: Q27279286
• Mol file: 160194-39-8.mol

Synonyms:160194-39-8;Des(dimethylamino)hydroxyrizatriptan;2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethanol;2-(5-((1H-1,2,4-Triazol-1-yl)methyl)-1H-indol-3-yl)ethanol;GUF1804OA0;2-(5-[1,2,4]Triazol-1-ylmethyl-1H-indol-3-yl)-ethanol;1H-Indole-3-ethanol, 5-(1H-1,2,4-triazol-1-ylmethyl)-;2-(5-(1H-1,2,4-Triazol-1-ylmethyl)-1H-indol-3-yl)ethanol;2-(5-((1H-1,2,4-triazol-1-yl)methyl)-1H-indol-3-yl)ethan-1-ol;2-{5-[(1H-1,2,4-triazol-1-yl)methyl]-1H-indol-3-yl}ethan-1-ol;5-(1H-1,2,4-triazol-1-ylmethyl)-1H-Indole-3-ethanol;UNII-GUF1804OA0;Rizatriptan benzoate impurity F [EP];SCHEMBL4344147;DTXSID20166834;WXWBRTKSGCYLQS-UHFFFAOYSA-N;2-[5-(1,2,4-Triazol-1-ylmethyl)-1H-indol-3-yl]ethyl alcohol;MFCD03840590;CS-0340423;FT-0731877;A899332;Q27279286;RIZATRIPTAN BENZOATE IMPURITY F [EP IMPURITY]

Chemical Property of Des(dimethylamino)hydroxyrizatriptan

Chemical Property:

• Boiling Point: 545.458 °C at 760 mmHg
• PKA: 14.95±0.10(Predicted)
• Flash Point: 283.683 °C
• PSA: 66.73000
• Density: 1.357g/cm³
• LogP: 1.34250
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 242.11676108
• Heavy Atom Count: 18
• Complexity: 276

Purity/Quality:

99.9% ^*data from raw suppliers

2-(5-[1,2,4]Triazol-1-ylmethyl-1H-indol-3-yl)-ethanol 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1CN3C=NC=N3)C(=CN2)CCO
• Uses: 5-(1H-1,2,4-Triazol-1-ylmethyl)-1H-indole-3-ethanol is an intermediate in the synthesis of Rizatriptan Benzoate (R545000); a selective serotonin 5-HT1D receptor agonist and a potential anti-migraine drug.

Technology Process of Des(dimethylamino)hydroxyrizatriptan

There total 3 articles about Des(dimethylamino)hydroxyrizatriptan 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:

4-(1H-1,2,4-triazol-1-ylmethyl)aniline (119192-10-8) → 2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethyl alcohol (160194-39-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / ICl, CaCO₃ / methanol; H₂O

2: 1.) 2 molpercent Pd(OAc)2, Na₂CO₃; 2.) HCl / 1.) DMF, 100 deg C; 2.) MeOH

With hydrogenchloride; palladium diacetate; Iodine monochloride; sodium carbonate; calcium carbonate; In methanol; water;

DOI:10.1016/0040-4039(94)88204-5

Reference yield:

1-triethylsilanyl-4-(triethylsilanyloxy)but-1-yne (160194-28-5) + 4-((1H-1,2,4-triazol-1-yl)methyl)-2-iodobenzenamine (160194-26-3) → 2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethyl alcohol (160194-39-8)

Guidance literature:

With hydrogenchloride; palladium diacetate; sodium carbonate; Yield given. Multistep reaction; 1.) DMF, 100 deg C; 2.) MeOH;

DOI:10.1016/0040-4039(94)88204-5

Reference yield:

→ 2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethyl alcohol (160194-39-8)

Guidance literature:

upstream raw materials:

1-triethylsilanyl-4-(triethylsilanyloxy)but-1-yne

4-((1H-1,2,4-triazol-1-yl)methyl)-2-iodobenzenamine

4-(1H-1,2,4-triazol-1-ylmethyl)aniline

Downstream raw materials:

rizatriptan

rizatriptan benzoate