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942070-38-4

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  • 1-tert-Butyl 2-methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1,2-dicarboxylate;942070-38-4

    Cas No: 942070-38-4

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  • Amadis Chemical Co., Ltd.
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942070-38-4 Usage

Description

1-BOC-2-(methoxycarbonyl)pyrrole-4-boronic acid is a boronic acid derivative with the molecular formula C13H16BNO5. It features a pyrrole ring with a BOC (tert-butyloxycarbonyl) protecting group at the 1-position and a methoxycarbonyl group at the 2-position. 1-BOC-2-(methoxycarbonyl)pyrrole-4-boronic acid, is a versatile building block in organic synthesis, particularly for the preparation of pyrrole-containing compounds such as pharmaceuticals and agrochemicals.

Uses

Used in Organic Synthesis:
1-BOC-2-(methoxycarbonyl)pyrrole-4-boronic acid is used as a building block for the synthesis of various pyrrole-containing compounds. Its unique structure allows for the selective and mild formation of carbon-carbon bonds, making it a valuable tool in the field of organic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-BOC-2-(methoxycarbonyl)pyrrole-4-boronic acid is used as a key intermediate for the development of novel therapeutic agents. Its pyrrole core is a common structural motif in many bioactive molecules, and its functional groups can be further modified to enhance the pharmacological properties of the resulting compounds.
Used in Agrochemical Industry:
1-BOC-2-(methoxycarbonyl)pyrrole-4-boronic acid is also used in the agrochemical industry for the synthesis of bioactive compounds with potential applications in crop protection and pest control. Its unique structure and reactivity make it a promising candidate for the development of new agrochemicals with improved efficacy and selectivity.
Used as a Ligand in Metal-Catalyzed Cross-Coupling Reactions:
1-BOC-2-(methoxycarbonyl)pyrrole-4-boronic acid can be used as a ligand in metal-catalyzed cross-coupling reactions, facilitating the formation of carbon-carbon bonds between different organic molecules. This application expands its utility in the synthesis of complex organic compounds and contributes to the advancement of organic chemistry.
Used as a Reagent for the Functionalization of Aromatic Compounds:
Furthermore, 1-BOC-2-(methoxycarbonyl)pyrrole-4-boronic acid serves as a reagent for the functionalization of aromatic compounds. Its boronic acid functionality allows for the selective modification of aromatic rings, enabling the synthesis of diverse aromatic derivatives with potential applications in various fields, including materials science, pharmaceuticals, and agrochemicals.

Check Digit Verification of cas no

The CAS Registry Mumber 942070-38-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 9,4,2,0,7 and 0 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 942070-38:
(8*9)+(7*4)+(6*2)+(5*0)+(4*7)+(3*0)+(2*3)+(1*8)=154
154 % 10 = 4
So 942070-38-4 is a valid CAS Registry Number.

942070-38-4Relevant articles and documents

Synthesis of Novel Pyrazine-Substituted 1 H -Pyrrole-2-carboxamides and Related Tethered Heterocycles

Borrows, Rachel,Fairley, Gary,Feron, Lyman J. L.,Grant, Emma,Greenwood, Ryan D. R.,Howells, Rachel L.,Hughes, Samantha,Lamont, Scott G.,Lenz, Eva,McGuire, Thomas M.,Simpson, Iain

, (2022/02/10)

As part of a drug discovery program, 4-pyrazin-2-yl-1H-pyrrole-2-carboxamides were accessed along with a number of bicyclic analogues. Routes to these compounds were largely absent from the scientific literature. The synthesis of a 4-(pyrazin-2-yl)-1H-pyrrole-2-carboxamide and several fused bicyclic analogues all using standard procedures (SNAr, borylation, C C cross couplings, hydrolysis, amide bond formation, cyclisation, halogenation, and alkylation) from readily available starting materials is reported. The synthetic sequences range from 4-2 steps per final compound, with yields of isolated intermediates ranging from 20 to ?100%.

Discovery of a Potent and Selective Oral Inhibitor of ERK1/2 (AZD0364) That Is Efficacious in Both Monotherapy and Combination Therapy in Models of Nonsmall Cell Lung Cancer (NSCLC)

Ward, Richard A.,Anderton, Mark J.,Bethel, Paul,Breed, Jason,Cook, Calum,Davies, Emma J.,Dobson, Andrew,Dong, Zhiqiang,Fairley, Gary,Farrington, Paul,Feron, Lyman,Flemington, Vikki,Gibbons, Francis D.,Graham, Mark A.,Greenwood, Ryan,Hanson, Lyndsey,Hopcroft, Philip,Howells, Rachel,Hudson, Julian,James, Michael,Jones, Clifford D.,Jones, Christopher R.,Li, Yongchao,Lamont, Scott,Lewis, Richard,Lindsay, Nicola,McCabe, James,McGuire, Thomas,Rawlins, Philip,Roberts, Karen,Sandin, Linda,Simpson, Iain,Swallow, Steve,Tang, Jia,Tomkinson, Gary,Tonge, Michael,Wang, Zhenhua,Zhai, Baochang

supporting information, p. 11004 - 11018 (2019/12/02)

The RAS/MAPK pathway is a major driver of oncogenesis and is dysregulated in approximately 30% of human cancers, primarily by mutations in the BRAF or RAS genes. The extracellular-signal-regulated kinases (ERK1 and ERK2) serve as central nodes within this pathway. The feasibility of targeting the RAS/MAPK pathway has been demonstrated by the clinical responses observed through the use of BRAF and MEK inhibitors in BRAF V600E/K metastatic melanoma; however, resistance frequently develops. Importantly, ERK1/2 inhibition may have clinical utility in overcoming acquired resistance to RAF and MEK inhibitors, where RAS/MAPK pathway reactivation has occurred, such as relapsed BRAF V600E/K melanoma. We describe our structure-based design approach leading to the discovery of AZD0364, a potent and selective inhibitor of ERK1 and ERK2. AZD0364 exhibits high cellular potency (IC50 = 6 nM) as well as excellent physicochemical and absorption, distribution, metabolism, and excretion (ADME) properties and has demonstrated encouraging antitumor activity in preclinical models.

Synthetic strategies for the synthesis and transformation of substituted pyrrolinones as advanced intermediates for rhazinilam analogues

Kholod, Inga,Vallat, Olivier,Buciumas, Ana-Maria,Neels, Antonia,Neier, Reinhard

, p. 7865 - 7877 (2015/03/04)

The biaryl core structure of rhazinilam with its fixed dihedral angle is a pivotal element for its unique in vitro cytotoxic activity. Most of the related natural products are oxidized versions of rhazinilam. Replacing the sensitive pyrrole ring by a pyrrolinone ring is the basis of our initial strategy towards rhazinilam analogues. With this goal, variants of the sequence crossed Mukaiyama aldol reaction followed by the Staudinger reaction were studied. Reacting a suitably substituted acetophenone with O-methyl O-trimethylsilyl ketene acetal gave pyrrolinones 8a and 8b in good to excellent yields. These intermediates could be transformed in four high-yielding steps into the pyrrolic precursors 7a-c containing all the atoms necessary for the construction of rings A, B, and C of rhazinilam. Our studies illustrate a lack of stability of these intermediates. Alternative synthetic approaches towards this central biaryl core structure are described.

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