201929-00-2

Basic information

• Product Name: (2Z,4E)-5-(5,6-Dichloro-1H-indol-2-yl)-2-methoxy-N-(1,2,2,6,6-pentamethylpiperidin-4-yl)-2,4-pentadienamide
• Synonyms: SB-242784
• CAS NO: 201929-00-2
• Molecular Formula: C₂₄H₃₁Cl₂N₃O₂
• Molecular Weight: 464.43957
• Mol File: 201929-00-2.mol

Chemical Properties

• CAS DataBase Reference: (2Z,4E)-5-(5,6-Dichloro-1H-indol-2-yl)-2-methoxy-N-(1,2,2,6,6-pentamethylpiperidin-4-yl)-2,4-pentadienamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2Z,4E)-5-(5,6-Dichloro-1H-indol-2-yl)-2-methoxy-N-(1,2,2,6,6-pentamethylpiperidin-4-yl)-2,4-pentadienamide(201929-00-2)
• EPA Substance Registry System: (2Z,4E)-5-(5,6-Dichloro-1H-indol-2-yl)-2-methoxy-N-(1,2,2,6,6-pentamethylpiperidin-4-yl)-2,4-pentadienamide(201929-00-2)

Safety Data

• Hazardous Substances Data: 201929-00-2(Hazardous Substances Data)

Upstream product

• 40327-96-6 4-amino-1,2,2,6,6-pentamethylpiperidine 
• 180868-14-8 (2Z,4E)-5-(5,6-dichloro-2-indolyl)-2-methoxy-2,4-pentadienoic acid 

Relevant articles and documents

(2Z,4E)-5-(5,6-dichloro-2-indolyl)-2-methoxy-N-(1,2,2,6,6- pentamethylpiperidin-4-yl)-2,4-pentadienamide, a novel, potent and selective inhibitor of the osteoclast V-ATPase

Optimisation of a novel series of osteoclast ATPase inhibitors led to (2Z,4E)-5-(5,6-dichloro-2-indolyl)-2-methoxy-N-(1,2,2,6,6- pentamethylpiperidin-4-yl)-2,4-pentadienamide (1) that was the most potent compound in an in vitro osteoclast ATPase assay and in human bone resorption assays. Two of the possible geometric isomers have also been prepared and shown to be significantly less potent than 1.

Towards the synthesis of osteoclast inhibitor SB-242784

Osteoclast inhibitor SB-242784 (1) was prepared from pivotal indol intermediate 4. A 'Stille' cross coupling of organotin 2c with bromo acrylate 11 afforded diene 12 which was also obtained via a reduction-isomerization process of enyne 16. Bromoamide 3 was prepared from the corresponding acid 7 which was readily obtained from bromopyruvic acid.

Synthesis of 2-dienylindole, SB 242784, by a three-component palladium- catalyzed coupling reaction

The synthesis of SB 242784 using a novel one-pot Castro-Stephens-Suzuki reaction as the key reaction is described.