1-(5-(4-amino-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)indolin-1-yl)-2-(3-(trifluoromethyl)phenyl)ethanone

Base Information

• Chemical Name: 1-(5-(4-amino-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)indolin-1-yl)-2-(3-(trifluoromethyl)phenyl)ethanone
• CAS No.: 1337531-36-8
• Molecular Formula: C24H20F3N5O
• Molecular Weight: 451.451
• UNII: DPP2K6EFW8
• Nikkaji Number: J3.338.975B
• Wikipedia: GSK2606414
• Wikidata: Q15409439
• Pharos Ligand ID: 2GVXHHLL76MP
• ChEMBL ID: CHEMBL2171124
• Mol file: 1337531-36-8.mol

Synonyms:7-methyl-5-(1-((3-(trifluoromethyl)phenyl)acetyl)-2,3-dihydro-1H-indol-5-yl)-7H-pyrrolo(2,3-d)pyrimidin-4-amine;GSK2606414

Chemical Property of 1-(5-(4-amino-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)indolin-1-yl)-2-(3-(trifluoromethyl)phenyl)ethanone

Chemical Property:

• Boiling Point: 720.3±60.0 °C(Predicted)
• PKA: 5.76±0.30(Predicted)
• PSA: 77.04000
• Density: 1.43±0.1 g/cm3(Predicted)
• LogP: 5.01430
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 451.16199476
• Heavy Atom Count: 33
• Complexity: 721

Purity/Quality:

98% min ^*data from raw suppliers

GSK2606414 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=C(C2=C(N=CN=C21)N)C3=CC4=C(C=C3)N(CC4)C(=O)CC5=CC(=CC=C5)C(F)(F)F
• Uses: GSK 2606414 acts as a potent and selective inhibitor of protein kinase R and similarly endoplasmic reticulum kinase affecting numerous diseases such as cancer.

Technology Process of 1-(5-(4-amino-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)indolin-1-yl)-2-(3-(trifluoromethyl)phenyl)ethanone

There total 10 articles about 1-(5-(4-amino-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)indolin-1-yl)-2-(3-(trifluoromethyl)phenyl)ethanone 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: 75.0%

5-(2,3-dihydro-1H-indol-5-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine dihydrochloride (1337533-85-3) + 3-(trifluoromethyl)phenylacetic acid (351-35-9) → 1-[5-(4-amino-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2,3-dihydro-1H-indol-1-yl]-2-[3-(trifluoromethyl)phenyl]ethanone (1337531-36-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20 ℃; for 4.5h; Cooling with ice;

DOI:10.1021/jm300713s

Reference yield:

5-bromoindoline (22190-33-6) → 1-[5-(4-amino-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2,3-dihydro-1H-indol-1-yl]-2-[3-(trifluoromethyl)phenyl]ethanone (1337531-36-8)

Guidance literature:

Multi-step reaction with 5 steps

1: dmap / acetonitrile / 3 h / 20 °C

2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere

3: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; potassium phosphate monohydrate; tri tert-butylphosphoniumtetrafluoroborate / 1,4-dioxane; water / 1.5 h / 85 °C / Inert atmosphere

4: hydrogenchloride / water; ethanol / 5 h / 85 °C / Inert atmosphere

5: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 4.5 h / 20 °C / Cooling with ice

With hydrogenchloride; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium phosphate monohydrate; potassium acetate; N-ethyl-N,N-diisopropylamine; HATU; tri tert-butylphosphoniumtetrafluoroborate; In 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm300713s

Reference yield:

1,1-dimethylethyl 5-(4-amino-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2,3-dihydro-1H-indole-1-carboxylate (1391053-27-2) → 1-[5-(4-amino-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2,3-dihydro-1H-indol-1-yl]-2-[3-(trifluoromethyl)phenyl]ethanone (1337531-36-8)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / water; ethanol / 5 h / 85 °C / Inert atmosphere

2: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 4.5 h / 20 °C / Cooling with ice

With hydrogenchloride; N-ethyl-N,N-diisopropylamine; HATU; In ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jm300713s

upstream raw materials:

5-(2,3-dihydro-1H-indol-5-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine dihydrochloride

3-(trifluoromethyl)phenylacetic acid

5-bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Refernces

• 1、 Axten, Jeffrey M.,Medina, Jesús R.,Feng, Yanhong,Shu, Arthur,Romeril, Stuart P.,Grant, Seth W.,Li, William Hoi Hong,Heerding, Dirk A.,Minthorn, Elisabeth,Mencken, Thomas,Atkins, Charity,Liu, Qi,Rabindran, Sridhar,Kumar, Rakesh,Hong, Xuan,Goetz, Aaron,Stanley, Thomas,Taylor, J. David,Sigethy, Scott D.,Tomberlin, Ginger H.,Hassell, Annie M.,Kahler, Kirsten M.,Shewchuk, Lisa M.,Gampe, Robert T.. "Discovery of 7-methyl-5-(1-{[3-(trifluoromethyl)phenyl]acetyl}-2,3-dihydro- 1H-indol-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (GSK2606414), a potent and selective first-in-class inhibitor of protein kinase R (PKR)-like endoplasmic reticulum kinase (PERK)". . p. 7193 - 7207. Retrieved 2012/11/07.