Tag: M.W=200-250

Liu, Qingyun published the artcileBismuth(III)-Promoted Trifluoromethylthiolation of Pyrazolin-5-ones with Trifluoromethanesulfenamide, COA of Formula: C10H9ClN2O, the publication is ACS Omega (2017), 2(11), 7755-7759, database is CAplus and MEDLINE.

An efficient and facile method for the synthesis of trifluoromethylthiolated 5-hydroxy-1H-pyrazole derivatives by reaction of pyrazolin-5-ones with trifluoromethanesulfenamide (PhNHSCF₃) in the presence of BiCl₃ was developed.

ACS Omega published new progress about 14580-22-4. 14580-22-4 belongs to pyrazoles-derivatives, auxiliary class Organic Pigment, name is 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, and the molecular formula is C10H9ClN2O, COA of Formula: C10H9ClN2O.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Jiang, Jian-kang published the artcileDiscovery of 3-(4-sulfamoylnaphthyl)pyrazolo[1,5-a]pyrimidines as potent and selective ALK2 inhibitors, Synthetic Route of 1416437-27-8, the publication is Bioorganic & Medicinal Chemistry Letters (2018), 28(20), 3356-3362, database is CAplus and MEDLINE.

The pyrazolo[1,5-a]pyrimidine LDN-193189 is a potent inhibitor of activin receptor-like kinase 2 (ALK2) but is nonselective for highly homologous ALK3 and shows only modest kinome selectivity. Herein, we describe the discovery of a novel series of potent and selective ALK2 inhibitors by replacing the quinolinyl with a 4-(sulfamoyl)naphthyl, yielding ALK2 inhibitors that exhibit not only excellent discrimination vs. ALK3 but also high kinome selectivity. In addition, the optimized compound 23 demonstrates good ADME and in vivo pharmacokinetic properties.

Bioorganic & Medicinal Chemistry Letters published new progress about 1416437-27-8. 1416437-27-8 belongs to pyrazoles-derivatives, auxiliary class Other Aromatic Heterocyclic,Boronic acid and ester,Boronate Esters,Boronic acid and ester, name is 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyrimidine, and the molecular formula is C12H16BN3O2, Synthetic Route of 1416437-27-8.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Koike, Eiji published the artcileOrganic pigments. II. Syntheses of 1-phenyl-3-methyl-5-pyrazolone and its derivatives, Application In Synthesis of 14580-22-4, the publication is Nippon Kagaku Kaishi (1921-47) (1954), 56-8, database is CAplus.

cf. C.A. 48, 6388d, 11079a. Phenylhydrazine (I) (24 g.) was added within 30 min. to a mixture of 12 g. 60% EtOH and 29.2 g. AcCH₂CO₂Et (II) below 50掳, stirred for 2 hrs., then refluxed 4 hrs. and filtered to yield 35.5 g. of 1-phenyl-3-methyl-5-pyrazolone, m. 125.0-126.5掳. The treatment of 6.5 g. p-ClC₆H₄NHNH₂.HCl in H₂O, acidified with AcOH with 4.8 g. II gave 84% 1-(p-chlorophenyl)-3-methyl-5-pyrazolone, m. 165-6掳. Similarly were prepared the following analogs of III (1-substituent, m.p., % yield given): 慰-ClC₆H₄, 182-3掳, 68.6; m-ClC₆H₄, 124-5.5掳, 93.6; 慰-MeC₆H₄, 180-1掳, 26.6; m-MeC₆H₄, 104.7-5.0掳, 48; p-MeC₆H₄, 91.5-3.5掳, 43.6; p-MeOC₆H₄, 122-3掳, 36.7; m-O₂NC₆H₄, 185掳, 68.5; p-O₂NC₆H₄, 220掳, 80; m-HO₃SC₆H₄, 200掳, 90.8. AcCH₂CN (42 g.) in 54 cc. H₃O and 16 cc. concentrated HCl treated with 54 g. I in 200 cc. H₂O and 41 cc. HCl at 35-40掳, and further addition of 30 cc. concentrated HCl at 90掳 gave 62.5 g. of 1-phenyl-3-methyl-5-aminopyrazole, m. 110-111.5掳.

Nippon Kagaku Kaishi (1921-47) published new progress about 14580-22-4. 14580-22-4 belongs to pyrazoles-derivatives, auxiliary class Organic Pigment, name is 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, and the molecular formula is C10H9ClN2O, Application In Synthesis of 14580-22-4.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Wang, Yuting published the artcileDesign, synthesis, and biological evaluation of pyrano[2,3-c]pyrazole-Based RalA inhibitors against hepatocellular carcinoma, Computed Properties of 14580-22-4, the publication is Frontiers in Chemistry (Lausanne, Switzerland) (2021), 700956, database is CAplus and MEDLINE.

The discovery of a series of 6-sulfonylamide-pyrano[2,3-c]pyrazole derivatives I [R = H, 4-Me, 2-MeO, etc.; R¹ = C₆H₅, 4-MeC₆H₄, 4-MeOC₆H₄, etc.; R² = C₆H₅, 4-MeC₆H₄, 3-MeOC₆H₄, etc.] as novel RalA inhibitors was reported. ELISA-based biochem. assay results indicated that compounds I [R = H; R¹ = 4-MeC₆H₄, 4-MeOC₆H₄, 4-F₃CC₆H₄, 2,4-di-FC₆H₃, 2-thienyl; R² = 4-F₃CC₆H₄, 3-pyridyl, 4-pyridyl, 3-thienyl] suppressed RalA/B binding capacities to their substrates. Cellular proliferation assays indicated that these RalA inhibitors potently inhibited the proliferation of HCC cell lines, including HepG2, SMMC-7721, Hep3B, and Huh-7 cells. Among the evaluated compounds, compound I [R = H, R¹ = 4-MeOC₆H₄, R² = 4-F₃CC₆H₄] displayed good inhibitory capacities on RalA (IC₅₀ = 0.22渭M) and HepG2 cells (IC₅₀ = 2.28渭M). Overall, the results suggested that a novel small mol. RalA inhibitor with a 6-sulfonylamide-pyrano[2,3-c]-pyrazole scaffold suppressed autophagy and cell proliferation in hepatocellular carcinoma, and that it has potential for HCC-targeted therapy.

Frontiers in Chemistry (Lausanne, Switzerland) published new progress about 14580-22-4. 14580-22-4 belongs to pyrazoles-derivatives, auxiliary class Organic Pigment, name is 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, and the molecular formula is C3H6O2, Computed Properties of 14580-22-4.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Peng, Yingyuan published the artcilePd-Catalyzed intramolecular C-H activation and C-S formation to synthesize pyrazolo[5,1-b]benzothiazoles without an additional oxidant, SDS of cas: 14580-22-4, the publication is Organic Chemistry Frontiers (2019), 6(18), 3234-3237, database is CAplus.

An efficient synthesis of pyrazolo[5,1-b]benzothiazole scaffold via Pd-catalyzed intramol. C-H activation and C-S formation was reported. By starting from easily available 1-phenyl-1H-pyrazole-5-thiol compounds, a series of substituted pyrazolo[5,1-b]benzothiazoles were obtained with moderate to good yields. Interestingly, this reaction didn’t need any addnl. oxidant and the reaction conditions were also suitable for the synthesis of imidazo[2,1-b]benzothiazole derivatives

Organic Chemistry Frontiers published new progress about 14580-22-4. 14580-22-4 belongs to pyrazoles-derivatives, auxiliary class Organic Pigment, name is 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, and the molecular formula is C10H9ClN2O, SDS of cas: 14580-22-4.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Haessner, Rainer published the artcileCarbon-13 NMR data for chlorine- or nitro-substituted azomethine dyes, COA of Formula: C10H9ClN2O, the publication is Magnetic Resonance in Chemistry (1990), 28(9), 817-19, database is CAplus.

The ¹³C NMR of 1-aryl-substituted 3-methyl-2-pyrazolin-5-ones and their azomethine dyes have been recorded and assigned. Ortho substituents (Cl and NO₂) on the Ph ring in the 1-position of the pyrazoline moiety show a small influence on the chem. shift of the azomethine bond carbon atom, C-4.

Magnetic Resonance in Chemistry published new progress about 14580-22-4. 14580-22-4 belongs to pyrazoles-derivatives, auxiliary class Organic Pigment, name is 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, and the molecular formula is C10H9ClN2O, COA of Formula: C10H9ClN2O.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Hoeppner, F. D. published the artcileMO calculations for photographic dye development. VIII, Quality Control of 14580-22-4, the publication is Journal fuer Signalaufzeichnungsmaterialien (1975), 3(1), 75-7, database is CAplus.

The total 蟺 electronic energy, calculated using HMO-NBI formalism, was plotted versus the torsion angle, 胃. For R = H, a single min. in the total energy of I and II occurred at 胃鈭?0掳 while for III, the min. occurred at 胃鈭?5掳. The tautomer stability increased in the order III < I < II. For R = Cl, the potential curve showed two min. for each tautomer form, one at 胃 = 30-40掳 and the other at 胃 = 120-130掳, with a relatively high potential barrier; the relative stability of the tautomer did not change for R = Cl.

Journal fuer Signalaufzeichnungsmaterialien published new progress about 14580-22-4. 14580-22-4 belongs to pyrazoles-derivatives, auxiliary class Organic Pigment, name is 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, and the molecular formula is C10H9ClN2O, Quality Control of 14580-22-4.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Batezila, Giselle published the artcile(2-Chlorophenyl)-3-methylchromeno[2,3-c]pyrazol-4(1H)-one, SDS of cas: 14580-22-4, the publication is Molbank (2010), No pp. given, database is CAplus.

The title compound was prepared by treatment of 1-(2-chlorophenyl)-3-methyl-2-pyrazolin-5-one with 2-chlorobenzoyl chloride by using Ca(OH)₂ in 1,4-dioxane and subsequent cyclization of the thus obtained 4-aroyl-5-hydroxypyrazole with sodium hydride in dry DMF. Detailed spectroscopic data (¹H NMR, ¹³C NMR, ¹⁵N NMR, IR, MS) are presented.

Molbank published new progress about 14580-22-4. 14580-22-4 belongs to pyrazoles-derivatives, auxiliary class Organic Pigment, name is 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, and the molecular formula is C10H9ClN2O, SDS of cas: 14580-22-4.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Li, Chaomin published the artcileSulfone Displacement Approach for Large-Scale Synthesis of 4-Chloro-N-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-amine, Quality Control of 1462286-01-6, the publication is Organic Process Research & Development (2022), 26(1), 137-143, database is CAplus.

Route evaluation, process development, and large-scale manufacturing of title compound I were described. The improved route consists of two linear chem. steps: oxidation of 4-chloro-2-(methylthio)pyrimidine to 4-chloro-2-(methylsulfonyl)pyrimidine and displacement of the sulfonyl with N-(1-methyl-1H-pyrazol-4-yl)formamide under basic conditions followed by in situ hydrolysis of the N-formyl intermediate to deliver compound I. N-(1-Methyl-1H-pyrazol-4-yl)formamide was readily prepared from 1-methyl-1H-pyrazol-4-amine via reaction with formic acid.

Organic Process Research & Development published new progress about 1462286-01-6. 1462286-01-6 belongs to pyrazoles-derivatives, auxiliary class Pyrazoles, name is 4-Chloro-N-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-amine, and the molecular formula is C8H8ClN5, Quality Control of 1462286-01-6.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Wu, Xia published the artcileIodine-Catalyzed Oxidative Coupling To Construct C-O Bonds for the Synthesis of 2,3-Dihydrooxepines, Synthetic Route of 14580-22-4, the publication is Organic Letters (2017), 19(17), 4584-4587, database is CAplus and MEDLINE.

The iodine-catalyzed catalytic formal [3 + 3 + 1] cycloaddition for the preparation of a seven-membered O-heterocyclic ring is presented, which is an achievement of Me and carbonyl group reactivity of 3-methyl-5-pyrazolones to forge the C_sp3-O bond. This novel protocol provides a straightforward and efficient access to structurally diverse fused O-heterocycles through an iodine-catalyzed iodination/Kornblum oxidation/oxidative coupling/C-O bond formation cascade reaction. This approach demonstrates the unprecedented concurrent realization of the unique reactivity among the Me, methylene, and carbonyl groups in 3-methyl-5-pyrazolones for the construction of 2,3-dihydrooxepine rings. Moreover, a broad substrate scope displays a graceful diversity-oriented synthetic approach.

Organic Letters published new progress about 14580-22-4. 14580-22-4 belongs to pyrazoles-derivatives, auxiliary class Organic Pigment, name is 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, and the molecular formula is C5H5NO3S, Synthetic Route of 14580-22-4.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics