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Amines

Amines are a class of organic compounds containing a nitrogen atom with a lone pair of electrons.
They play a crucial role in a wide range of biological and chemical processes, ranging from neurotransmission to industrial applications.
Amimes are subdivided into primary, secondary, and tertiary amines based on the number of alkyl or aryl groups attached to the nitrogen.
These versatile compounds exhibit diverse properties and functionalities, making them an indispensable part of various research fields, including biochemistry, medicinal chemistry, and materials science.
Researchers can leverage the powerful AI-driven platform of PubCompare.ai to optimize their Amines research protocols, easily locate the best protocols from literature, pre-prints, and patents, and ensure reproducibility and accuracy through AI-powered comparisons.
By unlocking the power of PubCompare.ai, researchers can take their Amines research to new heights and drive advancements in their field.

Most cited protocols related to «Amines»

Constructing a Structure-Based Chemical Ontology from Existing Nomenclature

Each node or category name in ClassyFire’s chemical ontology or ChemOnt, was created by extracting common or existing chemical classification category terms from the scientific literature and available chemical databases. We used existing terms to avoid “reinventing the wheel”. By making use of commonly recognized or widely used terms that already exist in the chemical literature, we believed that the taxonomy (and the corresponding ontology) should be more readily adopted and understood. This dictionary creation process was iterative and required the manual review of a large number of specialized chemical databases, textbooks and chemical repositories. Because the same compounds can often be classified into multiple categories, an analysis of the specificity of each categorical term was performed. Those terms that were determined to be clearly generic (e.g. organic acid, organoheterocyclic compound) or described large numbers of known compounds were assigned to SuperClasses. Terms that were highly specific (e.g. alpha-imino acid or derivatives, yohimbine alkaloids) or which described smaller numbers of compounds that clearly fell within a larger SuperClass were assigned to Classes or SubClasses. This assignment also depended on their relationship to higher-level categories. In some cases multiple, equivalent terms were used to describe the same compounds or categories (imidazolines vs. dihydroimidazoles). To resolve these disputes, the frequency with which the competing terms were used was objectively measured (using Google page statistics or literature count statistics). Those having the highest frequency would generally take precedence. However, attention was also paid to the scientific community and expert panels. When available, the IUPAC term was used to name a specific category. Otherwise, if the experts clearly recommended a set of (less frequently used) terms, these would take precedence over terms initially chosen by our initial “popularity” selection criteria. Examples include the terms “Imidazolines” (229,000 Google hits) and “Dihydroimidazoles” (4590 Google hits). The other popular terms were then added as synonyms. A total of 9012 English synonyms were added to the ChemOnt terminology data set.
In a number of cases, new SuperClass and Class terms were created for chemical categories not explicitly defined in the literature. Of these, the resulting “novel” categories were typically constructed from the IUPAC nomenclature for organic and inorganic compounds. Because our chemical dictionary was built from extant or common terms, it contains many community-specific categories commonly used in the (bio-)chemical nomenclature (e.g. primary amines, steroids, nucleosides). Moreover, due to the diverse nature of active and biologically interesting compounds, many chemical categories linked to specific chemical activities or based on biomimetic skeletons (e.g. alpha-sulfonopeptides, piperidinylpiperidines) were added. For instance, several compounds from the category of imidazo[1,2-a]pyrimidines (CHEMONTID:0004377) have been shown to display GABA(A) antagonist activity, and a potential to treat anxiety disorders [35 (link)].
After all the dictionary terms were identified and compiled (4825 terms to date), each term was formally defined using a precise, yet easily understood text description that included the structural features corresponding to that chemical category (Fig. 3). These formal definitions and the corresponding category mappings formed the basis of the structural classification algorithm and the classification rules described below. Once defined, the terms in this Chemical Classification Dictionary were progressively added to the taxonomic structure to form the structure-based hierarchy underlying ClassyFire’s chemical classification scheme. With the combination of the taxonomic structure and the Chemical Classification Dictionary, ChemOnt can be formally viewed as an ontology (albeit purely a structural ontology).Fig. 3

The chemical taxonomy. The taxonomy is illustrated with the OBO-Edit software, showing definitions synonyms, references, and extended information

Djoumbou Feunang Y., Eisner R., Knox C., Chepelev L., Hastings J., Owen G., Fahy E., Steinbeck C., Subramanian S., Bolton E., Greiner R, & Wishart D.S. (2016). ClassyFire: automated chemical classification with a comprehensive, computable taxonomy. Journal of Cheminformatics, 8, 61.

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Publication 2016

Acids Alkaloids Amines Anxiety Disorders Attention Chemical Actions derivatives GABA Antagonists Generic Drugs Imidazolines Imino Acids Inorganic Chemicals Nucleosides Pyrimidines Skeleton Steroids Yohimbine

Molecular Dynamics Simulations of μOR

Simulations of the μ opioid receptor (μOR) were based on both the antagonist-bound inactive-state crystal structure (PDB ID: 4DKL) and the agonist-bound active-state crystal structure described in this manuscript. Coordinates were prepared by first removing all non-ligand and non-receptor molecules except for the cholesterol neighboring TM7 and for crystallographic water molecules near the receptor. For inactive μOR simulations, the T4 lysozyme was removed and acetyl and methylamide capping groups were placed on R263^ICL3 and E270^ICL3. For active μOR simulations, the nanobody was removed. In both cases, Prime (Schrödinger, Inc.) was used to model missing side-chains, and capping groups were then added to the N- and C- termini of the receptor. Histidine residues were simulated as the neutral Nε tautomer. Other titratable residues were simulated in their dominant protonation state at pH 7 except for D114^2.50, which was charged in inactive simulations and neutral in active simulations. A sodium ion was placed adjacent to D114^2.50 in inactive simulations.
The μOR was simulated in seven distinct conditions. These include: (1) The unliganded, inactive μOR, prepared by deleting the covalently bound, co-crystallized ligand, β-FNA, and adding a proton in its place to K233^5.39; (2) The inactive μOR with the co-crystallized ligand β-FNA; (3) The inactive μOR with agonist β-FOA (which does not bind covalently); (4) The unliganded, active μOR, prepared by deleting the co-crystallized ligand, BU72; (5) The active μOR with the co-crystallized ligand BU72; (6) The active μOR with the co-crystallized ligand BU72, with the N-terminal peptide deleted; (7) The active μOR with the antagonist BU74, with the N-terminal peptide deleted. Simulations of the active μOR without N-terminal peptide were prepared by deleting residues 52 through 64 of the receptor. Simulations with β-FOA were prepared by docking β-FOA to the crystallographic pose of β-FNA. Simulations with BU74 were prepared by docking BU74 to the crystallographic pose of BU72 and rotating the torsion angle of the methylcyclopropyl group to agree with that of β-FNA's methylcyclopropyl group.
We performed three to six simulations per condition (Supplementary Section). Simulations in a given condition were initiated from identical structures, but with initial atom velocities assigned independently and randomly.
It should be noted that in all liganded simulations, including those with β-FNA, β-FOA, BU72, and BU74, the ligand's tertiary amine nitrogen was protonated and therefore the ligand was simulated as a cation. This is necessary for the ligand to form the conserved salt bridge with neighboring D147^3.32.
Each of the resulting prepared μOR receptor structures was then aligned to the Orientations of Proteins in Membranes (OPM)^{52 (link)} entry for the inactive μOR using MacPyMOL (Schrödinger). The μOR was modified with disulfide bridges and inserted into a hydrated, equilibrated palmitoyloleoylphosphatidylcholine (POPC) bilayer using the CHARMM-GUI interface^{53 (link)-56 (link)}. Sodium and chloride ions were added to neutralize the system, reaching a final concentration of approximately 150 mM. All simulations contained one μOR receptor embedded in a lipid bilayer with 160 POPC molecules.

Huang W., Manglik A., Venkatakrishnan A.J., Laeremans T., Feinberg E.N., Sanborn A.L., Kato H.E., Livingston K.E., Thorsen T.S., Kling R., Granier S., Gmeiner P., Husbands S.M., Traynor J.R., Weis W.I., Steyaert J., Dror R.O, & Kobilka B.K. (2015). Structural insights into μ-opioid receptor activation. Nature, 524(7565), 315-321.

Publication 2015

1-palmitoyl-2-oleoylphosphatidylcholine Amines Chlorides Cholesterol Crystallography Disulfides Histidine Ions Ligands Lipid A Lipid Bilayers Membrane Proteins Mental Orientation Muramidase Nitrogen Peptides Protons Receptors, Opioid, mu Sodium Sodium Chloride

Compound Characterization and ADME Profiling

In-house Python scripts based on Openeye’s OEToolkit (Openeye, Santa Fe, USA) were used for compound manipulation and calculating descriptors for the number of heavy atoms, hydrogen-bond donors and acceptors, ring systems, and rotatable bonds. SD files provided by the suppliers were converted into SMILES strings. Protonation and tautomeric states of the compounds were standardised based on predefined substructure patterns to remove duplicates. In silico ADME parameters were calculated using ADMEnsa Interactive (BioFocus DPI, Saffron Walden, UK). Sybyl (Tripos, St. Louis, USA) was used to calculate ClogP values. Compounds containing groups that are charged at physiological pH were neutralised before calculating ClogP values. The ClogP values obtained for compounds where converted to clogD values by equation 1 and a pK_a of four was assumed for acetyl-sulfonamides, a pK_a of five for carboxylic acids and tetrazoles, a pK_a of six for aromatic thiols, and a pK_a of nine for amines.

Compounds and their descriptors were stored in a MySQL database and visualised using Vida and the Ogham package (Openeye).

Brenk R., Schipani A., James D., Krasowski A., Gilbert I.H., Frearson J, & Wyatt P.G. (2007). Lessons Learnt from Assembling Screening Libraries for Drug Discovery for Neglected Diseases. Chemmedchem, 3(3), 435-444.

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Publication 2007

Amines Carboxylic Acids Donors Hydrogen Bonds physiology Python Saffron Sulfhydryl Compounds Sulfonamides Tetrazoles

Comprehensive Bacterial Profiling with HOMIM Microarray

16S rRNA-based oligonucleotide reverse capture probes were custom synthesized ^††† with a 5’-(C6)-amine modified base, eight spacer thymidines and 18 to 20-nucleotides of target sequence, and printed (Michigan State University Research Technology Support Facility) on 25 × 76 mm aldehyde-coated glass slides ^‡‡‡. A total of 400 oligonucleotide probes targeting over 300 bacterial taxa ³³ (Table S1 in the supplemental material) were printed on each microarray. Probes targeting more than two closely related species appeared as clusters (37 altogether). Oral taxon designations for each species are provided as defined in the Human Oral Microbiome Database.³⁴ Included on each array were positive controls, i.e. “universal” probes that hybridize with all or most bacterial species, and provide both array orientation and labeling efficiency, as well as negative controls to determine array background levels. A universal 16S rRNA probe was also printed in a series of concentrations in order to monitor signal linearity. Moreover, probes were designed to have the same melting temperature (51–53°C), and G+C content. Regarding sensitivity, the lower limit of detection for the HOMIM array is about ≥ 10⁴ bacterial cells. Five copies of the array were printed per slide, each one printed as four 8 × 15 duplicate sub-arrays. Probes were arranged phylogenetically on each sub-array (Figure 1).

Colombo A.P., Boches S.K., Cotton S.L., Goodson J.M., Kent R., Haffajee A.D., Socransky S.S., Hasturk H., Van Dyke T.E, & Paster B.J. (2009). Comparisons of Subgingival Microbial Profiles of Refractory Periodontitis, Severe Periodontitis and Periodontal Health using the Human Oral Microbe Identification Microarray (HOMIM). Journal of periodontology, 80(9), 1421-1432.

Publication 2009

Aldehydes Amines Bacteria Base Sequence Cells Human Microbiome Hypersensitivity Microarray Analysis Oligonucleotide Probes RNA, Ribosomal, 16S Thymidine

Ligand Preparation for Molecular Docking

Ligands were prepared for docking using the Sybyl 7.3 Molecular Modeling Suite of Tripos, Inc. 3D conformations were generated using Concord 4.051 , hydrogen atoms were added and charges were loaded using the Gasteiger and Marsili charge calculation method.52 Basic amines were protonated and acidic carboxyl groups were de-protonated prior to charge calculation. The AMPPD ligand was minimized with the Tripos Force Field prior to docking using the Powell method with an initial Simplex53 optimization and 1000 iterations or gradient termination at 0.01 kcal/(mol*A). Input ligand file format was mol2 for all docking programs investigated.

Hevener K.E., Zhao W., Ball D.M., Babaoglu K., Qi J., White S.W, & Lee R.E. (2009). Validation of Molecular Docking Programs for Virtual Screening against Dihydropteroate Synthase. Journal of chemical information and modeling, 49(2), 444-460.

Publication 2009

3-(2'-spiroadamantane)-4-methoxy-4-(3''-phosphoryloxy)phenyl-1,2-dioxetane Acids Amines Hydrogen Ligands Rumex

Most recents protocols related to «Amines»

Synthesis of Oxadiazole-Piperidine Compound

Not available on PMC !

Example 30

[Figure (not displayed)]

To a stirred solution of 3-(3,4-dimethoxyphenyl)-5-(4-piperidyl)-1,2,4-oxadiazole (150 mg, 518 μmol) in N,N-dimethylformamide (1.50 mL) were added (2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate) (196 mg, 518 μmol), N-ethyl-N-(propan-2-yl)propan-2-amine (201 mg, 1.56 mmol, 271 μL), and 2-(benzylamino)acetic acid (89 mg, 544 μmol). The mixture was stirred at 20° C. for 16 h and filtered, and the crude filtrate was purified directly by prep-HPLC (column: Luna C8 100×30 5 μm; mobile phase: [water (10 mM ammonium carbonate)-acetonitrile]; B%: 30%-60%, 12 min) to give 2-(benzylamino)-1-[4-[3-(3,4-dimethoxyphenyl)-1,2,4-oxadiazol-5-yl]-1-piperidyl]ethanone (48 mg, 110 μmol, 21%) as a yellow solid. ¹H NMR (400 MHz, METHANOL-d4) δ=7.65 (dd, J=1.8, 8.2 Hz, 1H), 7.57 (d, J=1.8 Hz, 1H), 7.40-7.30 (m, 4H), 7.28-7.22 (m, 1H), 7.06 (d, J=8.4 Hz, 1H), 4.45 (br d, J=13.7 Hz, 1H), 3.94-3.83 (m, 7H), 3.78 (s, 2H), 3.57-3.44 (m, 2H), 3.40-3.33 (m, 1H), 3.27-3.20 (m, 1H), 3.01 (t, J=11.2 Hz, 1H), 2.17 (dd, J=2.8, 13.3 Hz, 2H), 1.93-1.73 (m, 2H); LCMS (ESI) m/z: [M+H]⁺=437.3.

US11873298B2. Compounds and uses thereof (2024-01-16). JANSSEN PHARMACEUTICA NV [BE]. Inventors: Matthew Lucas [US], Bertrand Le Bourdonnec [US], Iwona Wrona [US], Bhaumik Pandya [US], Parcharee Tivitmahaisoon [US], Kerem Ozboya [US], Benjamin Vincent [US], Daniel Tardiff [US], Jeff Piotrowski [US], Eric Solis [US], Robert Scannevin [US], Chee-Yeun Chung [US], Rebecca Aron [US], Kenneth Rhodes [US].

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Patent 2024

1H NMR Acetic Acid acetonitrile Amines ammonium carbonate Dimethylformamide High-Performance Liquid Chromatographies Lincomycin Methanol Oxadiazoles

Synthesis of Pyrrolidine Derivatives

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Example 26

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Synthesis of 169-A.

A mixture of tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (750 mg, 3.54 mmol), 1-methylpiperidin-4-one (800 mg, 7.08 mmol) and acetic acid (2 drops) in DCE (15 mL) was stirred at 50° C. for 2 h. Then Sodium triacetoxyborohydride (1.50 g, 7.08 mmol) was added into above mixture and stirred at 50° C. for another 2 h. After the reaction was completed according to LCMS, the solvent was diluted with water (10 mL) and then extracted by DCM (10 mL×3). The combined organics washed with brine (10 mL×3), dried over anhydrous Na₂SO₄and then concentrated in vacuo. The residue was purified by column chromatography on silica gel (DCM:MeOH=100:1˜50:1) to give 169-A (750 mg, 69%) as a yellow oil.

Synthesis of 169-B.

A solution of 169-A (400 mg, 1.29 mmol) in DCM (10 mL) was added TFA (5 mL) and stirred at room temperature for 1 h. when LCMS showed the reaction was finished. The solvent was removed in vacuo to give 169-B as a crude product and used to next step directly.

Synthesis of 169-C.

A mixture of 143-C (306 mg, 0.65 mmol) and 169-B (crude product from last step) in acetonitrile (6 mL) was stirred at 50° C. for 30 min. Then Na₂CO₃(624 mg, 6.50 mmol) was added into above mixture and stirred at 50° C. for 3 h. After the reaction was completed according to LCMS, the mixture was cooled to room temperature. The Na₂CO₃was removed by filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel (DCM:MeOH=100:1˜20:1) to give 169-C (230 mg, 76%) as a yellow solid.

Synthesis of 169.

A mixture of 169-C (230 mg, 0.49 mmol) and Pd/C (230 mg) in MeOH (10 mL) was stirred at room temperature for 30 min under H₂atmosphere. Pd/C was then removed by filtration through the Celite. The filtrate was concentrated and the residue was purified by Pre-TLC (DCM:MeOH=10:1) to give 169 (150 mg, 70%) as a white solid.

Compounds 152, 182, 199, 201, 202, 203, 235, 236 and 256 were synthesized in a similar manner using the appropriately substituted aldehyde or ketone variant of 169.

Compound 152.

50 mg, 36%, a light yellow solid.

Compound 182.

70 mg, 38%, a red solid.

Compound 199.

50 mg, 54%, a light yellow solid.

Compound 201.

30 mg, 42%, as a yellow solid.

Compound 202.

30 mg, 42%, a yellow solid.

Compound 203.

30 mg, 18%, a yellow solid.

Compound 235.

170 mg, 87%, a white solid.

Compound 236.

70 mg, 50%, a white solid.

Compound 256.

20 mg, 8%, a light yellow solid.

Compounds 210, 211, 215, 222, 223, 242 and 262 were synthesized in a similar manner using the appropriately substituted amine variant of 169.

Compound 210.

160 mg, 96%, a tan solid.

Compound 211.

70 mg, 40%, a white solid

Compound 215.

70 mg, 75%, a white solid.

Compound 222.

30 mg, 42%, a yellow solid.

Compound 223.

35 mg, 31%, a white solid.

Compound 242.

50 mg, 34%, a white solid.

Compound 262.

38 mg, 43%, a white solid.

US11858939B2. Hetero-halo inhibitors of histone deacetylase (2024-01-02). Alkermes, Inc. [US]. Inventors: Martin R. Jefson [US], John A. Lowe, III [US], Fabian Dey [CH], Andreas Bergmann [DE], Andreas Schoop [DE], Nathan Oliver Fuller [US].

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Patent 2024

Acetic Acid acetonitrile Aldehydes Amines Anabolism Atmosphere brine Celite Chromatography compound 26 compound 235 Filtration Ketones Light Lincomycin Pyrrole Silica Gel Sodium Solvents TERT protein, human

Synthesis of Pyrido[3,4-b]pyrazine Derivative

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Example 11

[Figure (not displayed)]

Step a: To a stirred suspension of 2,4-dichloro-6-methyl-3-nitropyridine (2.5 g, 12 mmol) in 24 mL of THE was added a solution of 7N NH₃in MeOH (14 mL, 98 mmol). After stirring for 3 h, the volatiles were removed in vacuo. The crude residue was purified by silica gel column chromatography to give 2-chloro-6-methyl-3-nitropyridin-4-amine. C₆H₇CN₃O₂[M+H]⁺ 188.0, found 188.0.

Step b: To a stirred mixture of 2-chloro-6-methyl-3-nitropyridin-4-amine (760 mg, 4.1 mmol) and Fe (1.1 g, 20 mmol) in a 5:1 solution of EtOH/H₂O (24 mL) was added 4.4 mL of conc. HCl. The contents were refluxed for 30 min, then cooled to room temperature and quenched with 100 mL of sat. NaHCO₃(aq). The mixture was extracted with EtOAc and the combined organic layers were dried over MgSO₄, filtered, and concentrated in vacuo to yield 2-chloro-6-methylpyridine-3,4-diamine. MS: (ES) m/z calculated for C₆H₉ClN₃[M+H]⁺ 158.0, found 158.0.

Step c: To a stirred solution of 2-chloro-6-methylpyridine-3,4-diamine (0.49 g, 3.1 mmol) in 3 mL of EtOH was added a 40% w/w aqueous solution of glyoxal (2.0 mL, 12 mmol). After refluxing for 16 h, the mixture was diluted with H₂O and extracted with EtOAc. The organic layers were combined, dried over MgSO₄, filtered and concentrated in vacuo. The crude residue was purified by silica gel column chromatography to give 5-chloro-7-methylpyrido[3,4-b]pyrazine. MS: (ES) m/z calculated for C₈H₇ClN₃[M+H]⁺ 180.0, found 180.1.

Step d: To a stirred solution of 5-chloro-7-methylpyrido[3,4-b]pyrazine (200 mg, 1.0 mmol) and 2′-chloro-2-methyl-3′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-3-amine (350 mg, 1.0 mmol) in 2 mL of MeCN was added AcOH (0.18 mL, 3.1 mmol). After 30 min, the volatiles were concentrated in vacuo. The crude residue was purified by silica gel column chromatography to give N-(2′-chloro-2-methyl-3′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-3-yl)-7-methylpyrido[3,4-b]pyrazin-5-amine. MS: (ES) m/z calculated for C₂₇H₂₉BClN₄O₂[M+H]⁺ 487.2, found 487.2.

Step e: To a stirred solution of N-(2′-chloro-2-methyl-3′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-3-yl)-7-methylpyrido[3,4-b]pyrazin-5-amine (390 mg, 0.66 mmol), 6-chloro-2-methoxynicotinaldehyde (240 mg, 1.4 mmol), and K₃PO₄(490 mg, 2.3 mmol) in a 1:1 solution of 1,4-dioxane/H₂O (3.3 mL) under N₂(g) was added Pd(PPh₃)₄(76 mg, 0.066 mmol). The mixture was stirred under N₂(g) at 90° C. for 3 h. The mixture was diluted with H₂O and then extracted with EtOAc. The combined organic layers were dried over MgSO₄, filtered, and concentrated. The crude residue was purified by silica gel column chromatography to give 6-(2-chloro-2′-methyl-3′-((7-methylpyrido[3,4-b]pyrazin-5-yl)amino)-[1,1′-biphenyl]-3-yl)-2-methoxynicotinaldehyde. MS: (ES) m/z calculated for C₂₈H₂₃ClN₅O₂[M+H]⁺ 496.2, found 496.2.

Step f: To a stirred mixture of 6-(2-chloro-2′-methyl-3′-((7-methylpyrido[3,4-b]pyrazin-5-yl)amino)-[1,1′-biphenyl]-3-yl)-2-methoxynicotinaldehyde (120 mg, 0.25 mmol), (S)-5-(aminomethyl)pyrrolidin-2-one hydrochloride (150 mg, 0.99 mmol), and trimethylamine (0.14 mL, 0.99 mmol) in a 4:1 solution of DCM/MeOH (5 mL) was added NaBH(OAc)₃(530 mg, 2.5 mmol). After stirring for 30 min, the mixture was filtered through Celite, and the filtrate was concentrated in vacuo. The product was purified by preparative HPLC to give the product (S)-5-((((6-(2-chloro-2′-methyl-3′-((7-methylpyrido[3,4-b]pyrazin-5-yl)amino)-[1,1′-biphenyl]-3-yl)-2-hydroxypyridin-3-yl)methyl)amino)methyl)pyrrolidin-2-one. ¹H NMR (400 MHz, DMSO-d₆) δ 12.59 (s, 1H), 9.32 (s, 1H), 9.07 (d, J=2.0 Hz, 1H), 8.86 (d, J=2.0 Hz, 1H), 8.23 (d, J=8.7 Hz, 1H), 7.76 (d, J=7.0 Hz, 1H), 7.62 (s, 1H), 7.55 (d, J=7.5 Hz, 1H), 7.50-7.43 (m, 1H), 7.35 (dd, J=7.9, 7.9 Hz, 1H), 7.12 (s, 1H), 6.96 (d, J=7.5 Hz, 1H), 6.55 (s, 2H), 6.43 (d, J=7.1 Hz, 1H), 4.07 (s, 3H), 3.95-3.84 (m, 1H), 2.48 (s, 4H), 2.26-2.15 (m, 3H), 2.11 (s, 3H), 1.86-1.70 (m, 1H). MS: (ES) m/z calculated for C₃₂H₃₁ClN₇O₂[M+H]⁺ 580.2, found 580.1.

US11866429B2. Heteroaryl-biphenyl amines for the treatment of PD-L1 diseases (2024-01-09). CHEMOCENTRYX, INC. [US]. Inventors: Pingchen Fan [US], Christopher W. Lange [US], Rebecca M. Lui [US], Darren J. McMurtrie [US], Ryan J. Scamp [US], Ju Yang [US], Yibin Zeng [US], Penglie Zhang [US].

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Patent 2024

1H NMR 2-picoline 4-nitropyridine Amines Bicarbonate, Sodium Celite Chromatography Diamines Dioxanes diphenyl Ethanol Gel Chromatography Glyoxal High-Performance Liquid Chromatographies Pyrazines Silica Gel Silicon Dioxide Sulfate, Magnesium Sulfoxide, Dimethyl trimethylamine

Synthesis and Purification of Triazole-Indazole Derivatives

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Example 229

[Figure (not displayed)]

To a stirred solution of N-[5-[4-[(3-aminooxetan-3-yl)methoxy]phenyl]-1-tetrahydropyran-2-yl-1,2,4-triazol-3-yl]-1-tetrahydropyran-2-yl-indazol-5-amine (60 mg, 0.11 mmol) and N-[5-[4-[[3-(ethylamino)oxetan-3-yl]methoxy]phenyl]-1-tetrahydropyran-2-yl-1,2,4-triazol-3-yl]-1-tetrahydropyran-2-yl-indazol-5-amine (59 mg, 0.10 mmol) in dry DCM (3 mL) at r.t. under nitrogen was added trifluoroacetic acid (157.5 μL, 2.06 mmol) and the reaction stirred at 25° C. overnight. The mixture was purified by ion-exchange chromatography (SCX, eluting with 1 M NH₃in MeOH) and preparative HPLC (20-50% MeCN in H₂O) giving N-[5-[4-[[3-(ethylamino)oxetan-3-yl]methoxy]phenyl]-4H-1,2,4-triazol-3-yl]-1H-indazol-5-amine (10.9 mg, 0.02 mmol, 20% yield) as a white solid and N-[5-[4-[(3-aminooxetan-3-yl]methoxy]phenyl]-4H-1,2,4-triazol-3-yl]-1H-indazol-5-amine (19 mg, 0.04 mmol, 44% yield) as an off-white solid. Example 228: LC-MS (ES⁺, Method E): 4.25 min, m/z 378.1 [M+H]⁺. ¹H NMR (400 MHz, DMSO-d₆): δ 13.22 (s, 1H), 12.81 (s, 1H), 9.16 (s, 1H), 8.10 (s, 1H), 7.94 (d, J=2.5 Hz, 2H), 7.92 (s, 1H), 7.42 (d, J=1.5 Hz, 2H), 7.13 (d, J=9.0 Hz, 2H), 4.48 (d, J=6.0 Hz, 2H), 4.39 (d, J=6.0 Hz, 2H), 4.13 (s, 2H), 2.27 (s, 2H). Example 229: LC-MS (ES⁺, Method E): 4.44 min, m/z 405.9 [M+H]⁺. ¹H NMR (400 MHz, DMSO-d₆): δ 12.80 (s, 2H), 9.17 (s, 1H), 8.11 (t, J=1.5 Hz, 1H), 7.94 (s, 2H), 7.91 (d, J=2.5 Hz, 2H), 7.43-7.41 (m, 2H), 7.13 (d, J=9.0 Hz, 2H), 4.52 (d, J=6.0 Hz, 2H), 4.43 (d, J=6.0 Hz, 2H), 4.21 (s, 2H), 2.66-2.59 (m, 2H), 1.04 (t, J=7.0 Hz, 3H).

US11878020B2. Modulators of Rho-associated protein kinase (2024-01-23). Redx Pharma PLC [GB]. Inventors: Clifford D. Jones [GB], Peter Bunyard [GB], Gary Pitt [GB], Liam Byrne [GB], Thomas Pesnot [GB], Nicolas E. S. Guisot [GB].

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Patent 2024

1H NMR Amines High-Performance Liquid Chromatographies Indazoles Ion-Exchange Chromatographies Nitrogen Sulfoxide, Dimethyl Trifluoroacetic Acid

Synthesis of N-[2-[4-[3-(3,4-dimethoxyphenyl)-1,2,4-oxadiazol-5-yl]-1-piperidyl]-2-oxo-ethyl]-N-methyl-benzamide

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Example 22

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To a stirred solution of 3-(3,4-dimethoxyphenyl)-5-(4-piperidyl)-1,2,4-oxadiazole (150 mg, 518 μmol) in N,N-dimethylformamide (2 mL) was added (2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate) (196 mg, 518 μmol) and N-ethyl-N-(propan-2-yl)propan-2-amine (201 mg, 1.56 mmol, 271 μL) and 2-[benzoyl(methyl)amino]acetic acid (105 mg, 544 μmol). The mixture was stirred at 20° C. for 5 h, then cooled and purified directly by prep-HPLC (column: Luna C8 100×30 5 μm; mobile phase: [water (10 mM ammonium carbonate)-acetonitrile]; B%: 30%-60%, 12 min) to give N-[2-[4-[3-(3,4-dimethoxyphenyl) -1,2,4-oxadiazol-5-yl]-1-piperidyl]-2-oxo-ethyl]-N-methyl-benzamide (133 mg, 282 μmol, 54%) as a white solid. ¹H NMR (400 MHz, DMSO-d₆) δ=7.59 (dd, J=1.8, 8.4 Hz, 1H), 7.49-7.32 (m, 5H), 7.27 (br d, J=6.8 Hz, 1H), 7.16-7.08 (m, 1H), 4.44-4.24 (m, 2H), 4.21-4.03 (m, 1H), 4.02-3.88 (m, 1H), 3.88-3.74 (m, 6H), 3.56 (br d, J=13.7 Hz, 1H), 3.48-3.33 (m, 1H), 3.11-2.77 (m, 5H), 2.20-1.99 (m, 2H), 1.86 (br t, J=12.6 Hz, 1H), 1.74-1.48 (m, 2H), 1.43-1.26 (m, 1H); LCMS (ESI) m/z: [M+H]⁺=465.3.

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Patent 2024

1H NMR Acetic Acid acetonitrile Amines ammonium carbonate benzamide Dimethylformamide High-Performance Liquid Chromatographies Lincomycin N-methylbenzamide Oxadiazoles Sulfoxide, Dimethyl

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What are the different types of amines?

Amines are classified into three main types: primary, secondary, and tertiary amines. Primary amines have one alkyl or aryl group attached to the nitrogen atom, secondary amines have two, and tertiary amines have three. This structural variation leads to diverse properties and functionalities, making amines a versatile class of compounds used in a wide range of applications.

How can amines be used in various research fields?

Amines play a crucial role in numerous research fields, including biochemistry, medicinal chemistry, and materials science. In biochemistry, amines are involved in neurotransmission and other biological processes. In medicinal chemistry, amines are used in the development of pharmaceutical drugs. In materials science, amines are used in the synthesis of polymers and other advanced materials. The versatility of amines makes them an indispensable part of many research endeavors.

What are some common challenges in working with amines?

One common challenge in working with amines is ensuring reproducibility and accuracy in experimental protocols. Amines can be sensitive to factors like pH, temperature, and impurities, which can affect their reactivity and performance. Reasearchers may face difficulty in identifying the most effective protocols from the vast amount of literature available. Tis is where PubCompare.ai can be particularly helpful.

How can PubCompare.ai assist in optimizing Amines research?

PubCompare.ai's AI-driven platform can help researchers in several ways when working with amines. First, it allows you to efficiently screen protocol literature and identify the most relevant and effective protocols for your specific research goals. The platform's AI-powered analysis can highlight key differences in protocol effectiveness, enabling you to choose the best option for reproducibility and accuracy. By leveraging PubCompare.ai, you can take your amines research to new heights and drive advancements in your field.

More about "Amines"

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