N10-Didesmethyl Rizatriptan

Base Information

• Chemical Name: N10-Didesmethyl Rizatriptan
• CAS No.: 144035-23-4
• Molecular Formula: C13H15N5
• Molecular Weight: 241.296
• UNII: C8C2FFG5AN
• DSSTox Substance ID: DTXSID901211251
• Nikkaji Number: J1.269.295A
• Mol file: 144035-23-4.mol

Synonyms:N10-Didesmethyl Rizatriptan;144035-23-4;5-(1H-1,2,4-triazol-1-ylmethyl)-1h-indole-3-ethanamine;2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethanamine;2-{5-[(1H-1,2,4-triazol-1-yl)methyl]-1H-indol-3-yl}ethan-1-amine;C8C2FFG5AN;SCHEMBL7839523;DTXSID901211251;1H-Indole-3-ethanamine, 5-(1H-1,2,4-triazol-1-ylmethyl)-;5-(1H-1,2,4-Triazole-1-ylmethyl)-1H-indole-3-(ethanamine)

Chemical Property of N10-Didesmethyl Rizatriptan

Chemical Property:

• Boiling Point: 528.8±60.0 °C(Predicted)
• PKA: 16.95±0.30(Predicted)
• PSA: 72.52000
• Density: 1.35
• LogP: 2.00920
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Chloroform, Methanol
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 241.13274550
• Heavy Atom Count: 18
• Complexity: 272

Purity/Quality:

98%min ^*data from raw suppliers

N10-DidesmethylRizatriptan ^*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)CCN
• Uses: N10-Didesmethyl Rizatriptan is an intermediate in the synthesis of Rizatriptan (R545000) related compounds.

Technology Process of N10-Didesmethyl Rizatriptan

There total 6 articles about N10-Didesmethyl Rizatriptan 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: 38.0%

4-chlorobutanal dimethyl acetal (29882-07-3) + 4-(1,2,4-triazol-1-ylmethyl)phenylhydrazine (144035-22-3) → 2-<5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl>ethylamine (144035-23-4)

Guidance literature:

With hydrogenchloride; In ethanol; for 4h; Heating;

DOI:10.1021/jm00010a025

Reference yield:

1-(4-nitrophenyl)methyl-1,2,4-triazole (119192-09-5) → 2-<5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl>ethylamine (144035-23-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / H₂, 2N aq. HCl / 10percent Pd/C / ethanol; ethyl acetate / 0.2 h / 2068.6 Torr

2: 1.) aq. NaNO₂, conc. aq. HCl, 2.) SnCl₂*2H₂O, conc. aq. HCl / 1.) 0 deg C, 0.1 h, 2.) from -5 deg C to RT

3: 38 percent / 5N aq. HCl / ethanol / 4 h / Heating

With hydrogenchloride; hydrogen; tin(ll) chloride; sodium nitrite; palladium on activated charcoal; In ethanol; ethyl acetate;

DOI:10.1021/jm00010a025

Reference yield:

1-bromomethyl-4-nitro-benzene (100-11-8) → 2-<5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl>ethylamine (144035-23-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 52 percent / dimethylformamide / 16 h / 25 °C

2: 100 percent / H₂, 2N aq. HCl / 10percent Pd/C / ethanol; ethyl acetate / 0.2 h / 2068.6 Torr

3: 1.) aq. NaNO₂, conc. aq. HCl, 2.) SnCl₂*2H₂O, conc. aq. HCl / 1.) 0 deg C, 0.1 h, 2.) from -5 deg C to RT

4: 38 percent / 5N aq. HCl / ethanol / 4 h / Heating

With hydrogenchloride; hydrogen; tin(ll) chloride; sodium nitrite; palladium on activated charcoal; In ethanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00010a025

upstream raw materials:

4-chlorobutanal dimethyl acetal

4-(1,2,4-triazol-1-ylmethyl)phenylhydrazine

1-(4-hydrazinophenyl)-methyl-1,2,4-triazole dihydrochloride

1-(4-nitrophenyl)methyl-1,2,4-triazole

Downstream raw materials:

N-Benzyl-2[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethylamine

rizatriptan

Refernces

• 1、 Sarma, P. Seetharama,Rao, C. Nageswar,Surayanarayana,Reddy, Padi Pratap,Khalilluah,Praveen, Cherukupally. "Synthesis and characterization of potential impurities of the antimigraine drug, rizatriptan benzoate". . p. 603 - 612. Retrieved 2008/04/12.