329025-26-5

Basic information

• Product Name: 4-(3-broMophenyl)tetrahydro-2h-pyran-4-carboxaMide
• Synonyms: 4-(3-broMophenyl)tetrahydro-2h-pyran-4-carboxaMide;4-(3-bromophenyl)oxane-4-carboxamide;2H-PYRAN-4-CARBOXAMIDE, 4-(3-BROMOPHENYL)TETRAHYDRO-;4-(3-Bromophenyl)Tetrahydro-2H-Pyran-4-Carboxamide(WX633229)
• CAS NO: 329025-26-5
• Molecular Formula: C₁₂H₁₄BrNO₂
• Molecular Weight: 284.14906
• Mol File: 329025-26-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-(3-broMophenyl)tetrahydro-2h-pyran-4-carboxaMide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3-broMophenyl)tetrahydro-2h-pyran-4-carboxaMide(329025-26-5)
• EPA Substance Registry System: 4-(3-broMophenyl)tetrahydro-2h-pyran-4-carboxaMide(329025-26-5)

Safety Data

• Hazardous Substances Data: 329025-26-5(Hazardous Substances Data)

Upstream product

• 31938-07-5 (3-bromophenyl)acetonitrile 
• 245439-36-5 4-(3-Bromo-phenyl)-tetrahydro-pyran-4-carbonitrile 
• 371-42-6 4-Fluorothiophenol 

Downstream Products

• 329025-21-0 tetrahydro-4-[3-(4-fluorophenyl)-thio]phenyl-2H-pyran-4-carboxamide 
• 1029317-21-2 4-(3-([4-(1-methyl-1H-pyrazol-5-yl)phenyl]thio)phenyl)tetrahydro-2H-pyran-4-carboxamide 
• 1331755-98-6 C₂₄H₂₈N₂O₄S 
• 1029317-23-4 4-(3-(triisopropylsilylthio)phenyl)tetrahydro-2H-pyran-4-carboxamide 

Relevant articles and documents

BICYCLIC HETEROARYL AMINE COMPOUNDS AS PI3K INHIBITORS

Disclosed are compounds of Formula (I) or a salt thereof; wherein: X is N or CH; Q1 is: (i) C1, Br, I, -CN, -CH3, or -CF3; (ii) a 5-membered heteroaryl selected from pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, triazolyl, oxadiazolyl, and thiadiazolyl; (iii) a 6?membered heteroaryl selected from pyridinyl, pyridazinyl, and pyrimidinyl; or (iv) a bicyclic heteroaryl selected from indolyl, pyrrolopyridinyl, pyrazolopyridinyl and benzo[d]oxazolyl; wherein each of said 5-membered, 6-membered, and bicyclic heteroaryl is substituted with zero to 1 Ra and zero to 1 Rb; and R1, R2, R3, R4, R5, R6, Ra, and Rb are defined herein. Also disclosed are methods of using such compounds as modulators of PI3K, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing inflammatory and autoimmune diseases.

Development an efficient route to the 5-lipoxygenase inhibitor PF-04191834

A convergent six-step process for the synthesis of PF-04191834 (1), a potent and selective 5-lipoxygenase inhibitor, has been developed and used to deliver over 20 kg of API. The process uses the same bond-forming steps as the initial medicinal chemistry

PYRAZOLE DERIVATIVES AS 5-LO INHIBITORS

The invention relates to compounds of formula (I) processes for their preparation, their use as 5-lipoxygenase inhibitors and pharmaceutical compositions containing the same.

Development of a new variant of the migita reaction for carbon#sulfur bond formation used in the manufacture of tetrahydro-4-[3-[4-(2-methyl-1H-imidazol-1- yl)phenyl]thio]phenyl-2H-pyran-4-carboxamide

Palladium-catalyzed carbon-sulfur bond formation using modified Migita reaction conditions was explored and applied to the synthesis of a former antiasthma drug candidate, tetrahydro-4-[3-[4-(2-methyl-1H-imidazol-1-yl)phenyl] thio]phenyl-2H-pyran-4-carboxamide (5). The reaction was developed into a general method for thioaryl halide cross-coupling, and a specific example of its use to synthesize a key intermediate, tetrahydro-4-[3-(4-fluorophenyl)thio] phenyl-2H-pyran-4-carboxamide (6) was demonstrated at large scale to provide phase II clinical supplies of 5. Comparison of the multistep phase I process and the two-step phase II process showed an overall yield advantage over the bond-forming steps from common starting material (1) to API 5 of 40%. The ligand effect in the modified Migita reaction is described in detail. The second step of the scale-up process illustrated formation of carbon-nitrogen bonds without use of palladium catalysis, providing a contrast to the first reaction; both reactions were developed into efficient single-vessel direct isolation processes.

Pyrazole Analogs

The invention relates to the compounds of formula (I): or a pharmaceutically acceptable salt and solvate thereof, wherein R1 is F or H and to processes for the preparation of, intermediates used in the preparation of, compositions containing th

Process for making 5-lipoxygenase inhibitors having varied heterocyclic ring systems

process is described for preparing a compound of Formula (1.3.0): comprising: establishing a reaction mixture consisting of in an aprotic solvent; in the presence of a strong base in solid form selected from the group consisting of sodium hydroxide, NaOH;

Process for making 5-lipoxygenase inhibitors having varied heterocyclic ring systems

A novel process intermediate, tetrahydro-4-[3-(4-fluorophenyl)thio]phenyl-2H-pyran-4-carboxamide, of the formula: is described, as well as its use in a process of preparing 5-lipoxygenase inhibitors of the formula: which comprises establishing a reaction mixture consisting of: and an electron deficient monocyclic or benzo-fused bicyclic N-heterocycle containing two nitrogen atoms of the formula: ?in an aprotic solvent; in the presence of a carbonate of the formula: (M)2-CO3, where M is an alkali metal, Group 1/Ia element, selected from the group consisting of lithium, Li; sodium,Na; potassium, K; rubidium, Rb; and cesium, Cs; followed by heating of said reaction mixture under a nitrogen atmosphere; whereby there is produced the desired compound of the above-recited formula.