1391053-27-2

Basic information

• Product Name: 5-(1-tert-Butyloxycarbonyl-2,3-dihydro-1H-indol-5-yl)-7-Methyl-7H-pyrrolo[2,3-d]pyriMidin-4-aMine
• Synonyms: 5-(1-tert-Butyloxycarbonyl-2,3-dihydro-1H-indol-5-yl)-7-Methyl-7H-pyrrolo[2,3-d]pyriMidin-4-aMine;tert-Butyl5-{4-amino-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl}-2,3-dihydro-1H-indole-1-carboxylate;tert-Butyl 5-{4-amino-7-methyl-7H-pyrrolo[2,3-d]-pyrimidin-5-yl}-2,3-dihydro-1H-indole-1-carbo
• CAS NO: 1391053-27-2
• Molecular Formula: C20H23N5O2
• Molecular Weight: 365.42892
• Product Categories: Aromatics, Heterocycles, Indole Derivatives, Inhibitors, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 1391053-27-2.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 594.9±50.0 °C(Predicted)
• Appearance: /
• Density: 1.33±0.1 g/cm3(Predicted)
• Solubility: DMSO (Slightly, Heated), Methanol (Very Slightly)
• PKA: 5.76±0.30(Predicted)
• CAS DataBase Reference: 5-(1-tert-Butyloxycarbonyl-2,3-dihydro-1H-indol-5-yl)-7-Methyl-7H-pyrrolo[2,3-d]pyriMidin-4-aMine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(1-tert-Butyloxycarbonyl-2,3-dihydro-1H-indol-5-yl)-7-Methyl-7H-pyrrolo[2,3-d]pyriMidin-4-aMine(1391053-27-2)
• EPA Substance Registry System: 5-(1-tert-Butyloxycarbonyl-2,3-dihydro-1H-indol-5-yl)-7-Methyl-7H-pyrrolo[2,3-d]pyriMidin-4-aMine(1391053-27-2)

Safety Data

• Hazardous Substances Data: 1391053-27-2(Hazardous Substances Data)

Usage

Uses

Intermediate in the synthesis of GSK PERK Inhibitor (G797800).

Upstream product

• 862729-13-3 4-amino-5-iodo-7-methylpyrrolo[2,3‐d]pyrimidine 
• 837392-67-3 1,1-dimethylethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-indole-1-carboxylate 
• 1500-85-2 7-deazaadenine 
• 163622-50-2 4-amino-5-iodo-7H-pyrrolo[2,3‐d]pyrimidine 
• 1266343-30-9 5-bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine 
• 7781-10-4 4-Chlor-7-methyl-7H-pyrrolo<2,3-d>pyrimidin 
• 24424-99-5 di-tert-butyl dicarbonate 
• 261732-38-1 tert-butyl 5-bromoindoline-1-carboxylate 
• 22190-33-6 5-bromoindoline 
• 3680-69-1 4-chloro-1H-pyrrolo[2,3-d]pyrimidine 
• 1337532-51-0 5-bromo-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 

Downstream Products

• 1337531-51-7 5-{1-[(2,5-difluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1337531-26-6 5-{1-[(2-fluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1337531-27-7 5-{1-[(3-fluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1337531-86-8 5-{1-[(4-fluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1337531-25-5 7-methyl-5-{1-[(2-methylphenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1337531-29-9 7-methyl-5-{1-[(3-methylphenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1337531-39-1 5-{1-[(2-chlorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1337531-38-0 5-{1-[(3-chlorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1337531-42-6 7-methyl-5-(1-{[3-(methyloxy)phenyl]acetyl}-2,3-dihydro-1H-indol-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1337531-36-8 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 
• 1337531-89-1 1-[5-(4-Amino-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2,3-dihydro-1H-indol-1-yl]-2-[3-fluoro-5-(trifluoromethyl)phenyl]ethanone 
• 1337531-83-5 7-methyl-5-{1-[(2,3,5-trifluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7H-pyrrolo[2,3-d]pyrimidin-4-amine 

Relevant articles and documents

Identification of 5-(2,3-Dihydro-1 H-indol-5-yl)-7 H-pyrrolo[2,3- d]pyrimidin-4-amine Derivatives as a New Class of Receptor-Interacting Protein Kinase 1 (RIPK1) Inhibitors, Which Showed Potent Activity in a Tumor Metastasis Model

We herein report the structural optimization and structure-activity relationship studies of 5-(2,3-dihydro-1H-indol-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine derivatives as a new class of receptor-interacting protein kinase 1 (RIPK1) inhibitors. Among all obtained RIPK1 inhibitors, 1-(5-{4-amino-7-ethyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl}-2,3-dihydro-1H-indol-1-yl)-2-[3-(trifluoromethoxy)phenyl]ethan-1-one (22b) is the most active one. This compound potently inhibited RIPK1 with a binding affinity (KD) of 0.004 μM and an enzymatic IC50 value of 0.011 μM and also showed good kinase selectivity. It could efficiently protect cells from necroptosis and attenuate the necrotic cell death of vascular endothelial cells induced by tumor cells both in vitro and in vivo. Importantly, compound 22b exhibited excellent antimetastasis activity in the experimental B16 melanoma lung metastasis model. It also displayed favorable pharmacokinetic properties. Collectively, 22b could be a promising agent for preventing tumor metastasis.