851202-49-8

Basic information

• Product Name: BenzaMide, 4-[(3,3-diMethyl-1-oxobutyl)aMino]-3,5-difluoro-N-2-thiazolyl-
• Synonyms: BenzaMide, 4-[(3,3-diMethyl-1-oxobutyl)aMino]-3,5-difluoro-N-2-thiazolyl-;4-(3,3-dimethylbutanoylamino)-3,5-difluoro-N-(1,3-thiazol-2-yl)benzamide
• CAS NO: 851202-49-8
• Molecular Formula: C16H17F2N3O2S
• Molecular Weight: 353.3868864
• Mol File: 851202-49-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BenzaMide, 4-[(3,3-diMethyl-1-oxobutyl)aMino]-3,5-difluoro-N-2-thiazolyl-(CAS DataBase Reference)
• NIST Chemistry Reference: BenzaMide, 4-[(3,3-diMethyl-1-oxobutyl)aMino]-3,5-difluoro-N-2-thiazolyl-(851202-49-8)
• EPA Substance Registry System: BenzaMide, 4-[(3,3-diMethyl-1-oxobutyl)aMino]-3,5-difluoro-N-2-thiazolyl-(851202-49-8)

Safety Data

• Hazardous Substances Data: 851202-49-8(Hazardous Substances Data)

Upstream product

• 96-50-4 2-thiazolylamine 
• 201230-82-2 carbon monoxide 
• 1262897-92-6 N-(4-bromo-2,6-difluorophenyl)-3,3-dimethylbutyramide 
• 1262897-91-5 (2S,3S)-2-amino-3-methylpentanoic acid 2-[(E/Z)-4-(3,3-dimethylbutyrylamino)-3,5-difluorobenzoylimino]thiazol-3-ylmethyl ester hydrochloride 
• 913842-25-8 Lu AA₄₇₀₇₀ 
• 1423030-12-9 4-(3,3-dimethylbutanamido)-3,5-difluorobenzoic acid 

Relevant articles and documents

Efficient fluoride-catalyzed conversion of CO2 to CO at room temperature

A protocol for the efficient and selective reduction of carbon dioxide to carbon monoxide has been developed. Remarkably, this oxygen abstraction step can be performed with only the presence of catalytic cesium fluoride and a stoichiometric amount of a disilane in DMSO at room temperature. Rapid reduction of CO2 to CO could be achieved in only 2 h, which was observed by pressure measurements. To quantify the amount of CO produced, the reduction was coupled to an aminocarbonylation reaction using the two-chamber system, COware. The reduction was not limited to a specific disilane, since (Ph 2MeSi)2 as well as (PhMe2Si)2 and (Me3Si)3SiH exhibited similar reactivity. Moreover, at a slightly elevated temperature, other fluoride salts were able to efficiently catalyze the CO2 to CO reduction. Employing a nonhygroscopic fluoride source, KHF2, omitted the need for an inert atmosphere. Substituting the disilane with silylborane, (pinacolato)BSiMe2Ph, maintained the high activity of the system, whereas the structurally related bis(pinacolato)diboron could not be activated with this fluoride methodology. Furthermore, this chemistry could be adapted to 13C-isotope labeling of six pharmaceutically relevant compounds starting from Ba13CO 3 in a newly developed three-chamber system.

Effective palladium-catalyzed hydroxycarbonylation of aryl halides with substoichiometric carbon monoxide

A protocol for the Pd-catalyzed hydroxycarbonylation of aryl iodides, bromides, and chlorides has been developed using only 1-5 mol % of CO, corresponding to a pCO as low as 0.1 bar. Potassium formate is the only stoichiometric reagent, acting as a mildly basic nucleophile and a reservoir of CO. The substoichiometric CO could be delivered to the reaction from an acyl-Pd(II) precatalyst, which provides both the CO and an active catalyst, and thereby obviates the need for handling a toxic gas.

Discovery of phosphoric acid mono-{2-[(E/Z)-4-(3,3-dimethyl-butyrylamino)- 3,5-difluorobenzoylimino]-thiazol-3-ylmethyl} Ester (Lu AA47070): A phosphonooxymethylene prodrug of a potent and selective hA2A receptor antagonist

The discovery and structure-activity relationship of a series of hA 2A receptor antagonists is described. Compound 28 was selected from the series as a potent and selective compound and was shown to be efficacious in an in vivo model of Parkinson's disease. It had acceptableADME properties; however, the low intrinsic solubility of this compound was limiting for its developability, because the oral bioavailability from dosing in suspension was significantly lower than the oral bioavailability from solution dosage. As a consequence, prodrugs of 28 were prepared with dramatically increased aqueous solubility. The prodrugs efficiently delivered 28 into systemic circulation, with no detectable levels of prodrug in plasma samples. From this investigation, we selected 32 (Lu AA47070), a phosphonooxymethylene prodrug of 28, as a drug candidate.

PRO-DRUGS OF N-THIAZOL-2YL-BENZAMIDE DERIVATIVES

The invention relates to compounds of the formula I wherein the variables are as defined in the claims. The compounds are pro-drugs of A2A-receptor ligands with improved aqueous solubility, and are useful in the treatment of neurological and psychiatric disorders where an A2A-receptor is implicated.

N-THIAZOL-2-YL-BENZAMIDE DERIVATIVES

The invention relates to N-thiazol-2-yl-benzamide derivatives of the formula I in the description wherein the variables are as defined in the claims. The compounds are A2A-receptor ligands, such as antagonists, agonists, reverse agonists or partial agonists, and are useful in the treatment of neurological and psychiatric disorders where an A2A-receptor is implicated.