Urea, N-((1R)-5-(1,1-dimethylethyl)-2,3-dihydro-1H-inden-1-yl)-N'-1H-indazol-4-yl-

Base Information

• Chemical Name: Urea, N-((1R)-5-(1,1-dimethylethyl)-2,3-dihydro-1H-inden-1-yl)-N'-1H-indazol-4-yl-
• CAS No.: 808756-71-0
• Deprecated CAS: 1083090-71-4
• Molecular Formula: C21H24N4O
• Molecular Weight: 348.448
• UNII: J0YBN3USJN
• ChEMBL ID: CHEMBL398338
• DSSTox Substance ID: DTXSID801001609
• Pharos Ligand ID: 1QBRAAL5H2A7
• Wikidata: Q72503428
• Mol file: 808756-71-0.mol

Synonyms:ABT 102;ABT-102;ABT102

Chemical Property of Urea, N-((1R)-5-(1,1-dimethylethyl)-2,3-dihydro-1H-inden-1-yl)-N'-1H-indazol-4-yl-

Chemical Property:

• Vapor Pressure: 2.68E-11mmHg at 25°C
• Refractive Index: 1.656
• Boiling Point: 529.5 °C at 760 mmHg
• Flash Point: 274.1 °C
• PSA: 69.81000
• Density: 1.24 g/cm³
• LogP: 5.13330
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 348.19501140
• Heavy Atom Count: 26
• Complexity: 517

Purity/Quality:

99% ^*data from raw suppliers

ABT-102 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C1=CC2=C(C=C1)C(CC2)NC(=O)NC3=CC=CC4=C3C=NN4
• Isomeric SMILES: CC(C)(C)C1=CC2=C(C=C1)[C@@H](CC2)NC(=O)NC3=CC=CC4=C3C=NN4
• Recent ClinicalTrials: A Safety, Tolerability and Pharmacokinetic Study of ABT-102 in Healthy Subjects

Technology Process of Urea, N-((1R)-5-(1,1-dimethylethyl)-2,3-dihydro-1H-inden-1-yl)-N'-1H-indazol-4-yl-

There total 8 articles about Urea, N-((1R)-5-(1,1-dimethylethyl)-2,3-dihydro-1H-inden-1-yl)-N'-1H-indazol-4-yl- 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:

(R)-1-(2-benzyl-2H-indazol-4-yl)-3-(5-tert-butyl-2,3-dihydro-1H-indan-1-yl)urea (952734-48-4) → N-[(1R)-5-tert-butyl-2,3-dihydro-1H-inden-1-yl]-N'-1H-indazol-4-ylurea (808756-71-0)

Guidance literature:

With formic acid; palladium(II) hydroxide/carbon; In tetrahydrofuran; water; at 60 ℃; for 3h;

Reference yield:

methyl 4-[({[(1R)-5-tert-butyl-2,3-dihydro-1H-inden-1-yl]amino}carbonyl)amino]-1H-indazole-1-carboxylate (808756-69-6) → N-[(1R)-5-tert-butyl-2,3-dihydro-1H-inden-1-yl]-N'-1H-indazol-4-ylurea (808756-71-0)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 0.5h;

DOI:10.1021/jm701007g

Reference yield:

tert-butylbenzene (253185-03-4,253185-04-5) → N-[(1R)-5-tert-butyl-2,3-dihydro-1H-inden-1-yl]-N'-1H-indazol-4-ylurea (808756-71-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: aluminum (III) chloride / dichloromethane / 0 - 5 °C / Inert atmosphere

1.2: Friedel-Crafts Acylation / 1.5 h / 0 - 5 °C / Inert atmosphere

2.1: ammonia

3.1: water; methanol / 1 h / 65 °C / Large scale

4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C

5.1: sodium hydroxide / methanol / 20 °C

With aluminum (III) chloride; ammonia; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In methanol; dichloromethane; water; N,N-dimethyl-formamide; 1.1: |Friedel-Crafts Acylation;

DOI:10.1021/op060228s

upstream raw materials:

(R)-1-(2-benzyl-2H-indazol-4-yl)-3-(5-tert-butyl-2,3-dihydro-1H-indan-1-yl)urea

methyl 4-[({[(1R)-5-tert-butyl-2,3-dihydro-1H-inden-1-yl]amino}carbonyl)amino]-1H-indazole-1-carboxylate

tert-butylbenzene

1-(4-(tert-butyl)phenyl)-3-chloropropan-1-one

Refernces

• 1、 -. "Process for the Preparation of Indazolyl Ureas that Inhibit Vanilloid Subtype1 (VR1) Receptors". Page/Page column 14. . Retrieved 2008/06/13.
• 2、 Lukin, Kirill,Hsu, Margaret C.,Chambournier, Gilles,Kotecki, Brian,Venkatramani,Leanna. "Development of a large scale asymmetric synthesis of vanilloid receptor (TRPV1) antagonist ABT-102". . p. 578 - 584. Retrieved 2012/12/31.