1268349-81-0

Basic information

• Product Name: 4-methyl-N-(1,2-oxazol-3-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide
• Synonyms: 4-methyl-N-(1,2-oxazol-3-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide
• CAS NO: 1268349-81-0
• Molecular Weight: 328.176
• Mol File: 1268349-81-0.mol

Chemical Properties

• CAS DataBase Reference: 4-methyl-N-(1,2-oxazol-3-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methyl-N-(1,2-oxazol-3-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide(1268349-81-0)
• EPA Substance Registry System: 4-methyl-N-(1,2-oxazol-3-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide(1268349-81-0)

Safety Data

• Hazardous Substances Data: 1268349-81-0(Hazardous Substances Data)

Upstream product

• 21900-33-4 3-bromo-4-methylbenzoyl chloride 
• 7697-26-9 3-bromo-4-methylbenzoic acid 
• 515131-35-8 4-methyl-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzoic acid 
• 1750-42-1 3-aminoisoxazole 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 1268346-48-0 3-(3-tert-butyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-6-yl)-4-methyl-N-(1,2-oxazol-3-yl)benzamide 
• 1190860-17-3 3-(4,4-Difluoro-2'-oxo-1',2'-dihydrospiro[cyclohexane-1,3'-indol]-6'-yl)-N-isoxazol-3-yl-4-methylbenzamide 
• 1190859-98-3 N-Isoxazol-3-yl-4-methyl-3-(2-oxo-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-pyran]-6-yl)benzamide 

Relevant articles and documents

2-OXO-2,3-DIHYDRO-1H-IMIDAZO[4,5-B]PYRIDIN-6-YL)-4-METHYLBENZAMIDE DERIVATIVES AND SIMILAR COMPOUNDS AS RIPK2 INHIBITORS FOR TREATING E.G. AUTOIMMUNE DISEASES

Disclosed are compounds of Formula 1, and pharmaceutically acceptable salts thereof, wherein α, β, R2, R3, R4, R5, R8, R9, X1, X6, and X7 are defined in the specification. The compounds of formula 1 are receptor-interacting protein kinase 2 (RIPK2) inhibitors for treating e.g. type I hypersensitivity reactions, autoimmune diseases, inflammatory disorders, cancer and non-malignant proliferative disorders, such as e.g. allergic rhinitis, asthma, atopic dermatitis, rheumatoid arthritis, multiple sclerosis, systemic lupus erythematosus, lupus nephritis, psoriasis, immune thrombocytopenic purpura, inflammatory bowel disease, chronic obstructive pulmonary disease, Sjogren's syndrome, ankylosing spondylitis, Behcet's disease, graft versus host disease, pemphigus vulgaris, idiopathic plasmacytic lymphadenopathy, atherosclerosis, myocardial infarction and thrombosis. The present description discloses the preparation of exemplary compounds as well as pharmacological data thereof (e.g. pages 107 to 208; examples 1 to 109; table 1). An exemplary compound is e.g. N-cyclopropyl-2-fluoro-5-(l-(2-fluoroethyl)-3-(l-hydroxy-2-methylpropan-2-yl)-2-oxo-2,3-dihydro-lH-imidazo[4,5-b]pyridin-6-yl)-4-methylbenzamide (example 1).

Structure-Based Design, Synthesis, and Biological Evaluation of Imidazo[4,5-b]Pyridin-2-one-Based p38 MAP Kinase Inhibitors: Part 2

We identified novel potent inhibitors of p38 mitogen-activated protein (MAP) kinase using a structure-based design strategy, beginning with lead compound, 3-(butan-2-yl)-6-(2,4-difluoroanilino)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1). To enhance the inhibitory activity of 1 against production of tumor necrosis factor-α (TNF-α) in human whole blood (hWB) cell assays, we designed and synthesized hybrid compounds in which the imidazo[4,5-b]pyridin-2-one core was successfully linked with the p-methylbenzamide fragment. Among the compounds evaluated, 3-(3-tert-butyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-6-yl)-4-methyl-N-(1-methyl-1H-pyrazol-3-yl)benzamide (25) exhibited potent p38 inhibition, superior suppression of TNF-α production in hWB cells, and also significant in vivo efficacy in a rat model of collagen-induced arthritis (CIA). In this paper, we report the discovery of potent, selective, and orally bioavailable imidazo[4,5-b]pyridin-2-one-based p38 MAP kinase inhibitors.