Category: 3553-12-6

De Mendoza Sans, Javier published the artcileSynthesis of N-non-substituted 3(5)-hydrazino pyrazoles, Quality Control of 3553-12-6, the publication is Revista de la Real Academia de Ciencias Exactas, Fisicas y Naturales de Madrid (1971), 65(4), 739-839, database is CAplus.

A thesis with 68 references (5)-Amino-4-(ethoxycarbonyl)pyrazole (I) was hydrolyzed and decarboxylated to give 80% 3(5)-amino-pyrazole. I was diazotized and reduced to the corresponding hydrazine. Similarly I was diazotized and coupled to β-naphthol in base to give the asym-triazine (II).

Revista de la Real Academia de Ciencias Exactas, Fisicas y Naturales de Madrid published new progress about 3553-12-6. 3553-12-6 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Amine,Amide, name is 3-Acetamidopyrazole, and the molecular formula is C5H7N3O, Quality Control of 3553-12-6.

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

Graubaum, Heinz published the artcileAcyl migrations on 3(5)-aminopyrazole, Recommanded Product: 3-Acetamidopyrazole, the publication is Journal fuer Praktische Chemie/Chemiker-Zeitung (1993), 335(7), 585-8, database is CAplus.

3-Aminopyrazole forms 3 isomeric monoacylation products [I–III, R = Me, Et, Ph, 4-Me₂CHC₆H₄, 4-ClC₆H₄], 4 diacylation products and 3 triacylation products by reaction with RNCO. Acetamides IV [R¹ = RNHCO, R = Me, Et, Ph; R¹ = C(:NH)OR², R² = 4-MeOC₆H₄, 4-MeC₆H₄, 4-ClC₆H₄] were obtained from 3-acetylaminopyrazole and RNCO or R²OCN. Acyl migrations are observed depending on the reaction temperature and the structure of the acyl residue.

Journal fuer Praktische Chemie/Chemiker-Zeitung published new progress about 3553-12-6. 3553-12-6 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Amine,Amide, name is 3-Acetamidopyrazole, and the molecular formula is C5H7N3O, Recommanded Product: 3-Acetamidopyrazole.

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

Makisumi, Yasuo published the artcileAzaindolizine compounds. X. Synthesis of 5,7-disubstituted pyrazolo[1,5-a]pyrimidines, Safety of 3-Acetamidopyrazole, the publication is Chemical & Pharmaceutical Bulletin (1962), 612-20, database is CAplus.

cf. CA 57, 16606b. The title compounds (I) were prepared in general by condensing AcCH₂CO₂Et (II), CH₂Ac₂ (III), NCCH₂CO₂Et (IV), and CH₂(CO₂Et)₂ (V) separately with 5-amino-pyrazole (VI), its 1-Ph derivative (VII), its 4-EtO₂C derivative (VIII), and its 4-NC. derivative (IX). II kept overnight at room temperature with VI, VII, or VIII in the absence of solvent gave the corresponding 5-EtO₂CCH:CMeNH derivatives (X-XII) of pyrazole, m. 102°, 80-1°, and 175-6°, resp. On the other hand, refluxing II with VI or VIII 2-2.5 hrs. in AcOH gave the cyclized compounds (Ia, R = H and EtO₂C), m. 298-9° and 218-20°, resp., whereas refluxing II 4 hrs. with VII in AcOH gave the different cyclized compound (XIII), m. 188-9°. Ia (R = H and EtO₂C) and XIII were formed also by refluxing X-XII 2-3 hrs. with AcOH. Ia (R = EtO₂C) was also formed by refluxing XI 10 hrs. with Na in EtOH, and Ia (R = H) was prepared by refluxing VI 3 hrs. with II in EtOH containing anhydrous ZnCl₂. Hydrolysis of 0.5 g. Ia (R = EtO₂C) by heating 2 hrs. on a steam bath with 10% NaOH yielded 0.45 g. corresponding free acid, m. 296-7° (decomposition), and this (0.5 g.) was successfully decarboxylated by refluxing 3 hrs. with 40% H₂SO₄ to yield 0.32 g. Ia (R = H). Also, 0.94 g. IX refluxed 2.5 hrs. with II in AcOH yielded 1.5 g. Ia (R = cyano), m. 313° (decomposition), and this (0.5 g.) hydrolyzed and decarboxylated by refluxing 4 hrs. with 40% H₂SO₄ also yielded 0.4 g. Ia (R = H). Refluxing III (in place of II) with VI or VIII 10-12 hrs. in EtOH containing 3 drops piperidine, removing the solvent, and purifying the residue by Al₂O₃ chromatography gave, resp., Ib (R = H), m. 40-40.5°, and Ib (R = EtO₂C), m. 107-7.5°. The latter, like Ia (R = EtO₂C) was hydrolyzed to the corresponding free acid, m. 178-9°, which was decarboxylated either by heating 20 min. at 200° without solvent or by refluxing with 40% H₂SO₄ to give Ib (R = H), formed likewise by refluxing the ester, Ib (R = EtO₂C), itself with 40% H₂SO₄. Use of IV (in place of II or III) with VI or VIII in EtOH containing Na gave, resp., Ic (R = H), m. 306° (decomposition), and Ic (R = EtO₂C), m. 236-7°, which was hydrolyzed to the free acid, m. 296° (decomposition), and this was decarboxylated by heating in vacuo at 260-70° to give Ic (R = H). However, heating IV with VI 2 hrs. at 160-70° in the absence of solvent gave the noncyclized 5-(2-cyanoacetamido)-pyrazole (XVI), m. 211-12° (decomposition), and this was cyclized to Ic (R = H) by heating 5 hrs. on a steam bath in AcOH. Finally, V (in place of II) with VI or VIII in EtOH containing Na gave, resp., Id (R = H), m. 239-40° (decomposition), and Id (R = EtO₂C), m. 186-7° (decomposition), which also was hydrolyzed to the corresponding acid, m. 229° (decomposition), and this heated 5 min. at 235° was not only decarboxylated but also decomposed to give 5-acetamidopyrazole (XV), m. 223-4°, identical with the product obtained by refluxing VI 1 hr. with AcOH. However, heating VI 15 min. on a steam bath with Ac₂O gave 1-acetyl-5-acetamidopyrazole, m. 190.5-1.5°, which was readily converted to XV by heating with H₂O. In support of the structures, ultraviolet absorption curves were shown for Ia (R = H, EtO₂C, and CN), X-XII, Ic (R = H), Id (R = H), XIV, and XV, and both infrared and ultraviolet absorption data were reported for most of the compounds The infrared spectra of I showed that the 5- or 7-HO groups were mainly in the lactam form, whereas the 5- or 7-H₂N groups kept the amino form in neutral medium, thus showing analogy with pyrimidine derivatives

Chemical & Pharmaceutical Bulletin published new progress about 3553-12-6. 3553-12-6 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Amine,Amide, name is 3-Acetamidopyrazole, and the molecular formula is C5H7N3O, Safety of 3-Acetamidopyrazole.

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

Reimlinger, Hans K. published the artcile3(5)-Diazopyrazole, Application In Synthesis of 3553-12-6, the publication is Chemische Berichte (1961), 1036-41, database is CAplus.

3(5)-Aminopyrazole (I) prepared from pyrazole-3(5)-carboxylic acid hydrazide (II) gave with iso-AmONO the diazonium chloride (III). The diazotization in weakly acidic solution yielded the diazoamino compound III was converted in weakly alk. solution to the CHCl₃-soluble unstable 3(5)-diazopyrazole (IV). III and IV gave with HI the 3(5)-iodopyrazole (V) and with 2-C₁₀H₇OH (VI) an O-free coupling product. Et 3(5)-pyrazolecarboxylate (342 g.) (from 300 g. N₂CHCO₂Et and C₂H₂) in 200 g. anhydrous N₂H₄ heated 8 h. on the water bath and evaporated in vacuo yielded 390 g. II, m. 166-8° (MeOH). II (390 g.) in 2.5 l. 2N HCl treated with stirring at 0° with solid NaNO₂ in small portions gave 340 g. pyrazole-3(5)-carboxylic acid azide (VII), m. 158-60°. VII (340 g.) in 500 cc. absolute EtOH heated 24 h. on the water bath gave 299 g. Et N-[3(5)-pyrazolyl]urethane (VIII), m. 155-7° (MeOH). VIII (299 g.) and 920 g. Ba(OH)₂.8H₂O in 1.6 l. H₂O refluxed 36 h., filtered, concentrated to half-volume, and extracted continuously with Et₂O yielded 127 g. I, b_1.5 115-16°, m. 38-40°. VIII (10 g.), 20 cc. concentrated HCl, and 10 cc. AcOH refluxed 10 h., evaporated in vacuo, the viscous residue dissolved in saturated aqueous Na₂CO₃, and the solution extracted continuously with Et₂O yielded 5.3 g. N-Ac derivative of I, m. 22-3° (dioxane). I (3 g.) in 150 cc. MeOH saturated at 0° with HCl, filtered, the residue in 100 cc. MeOH treated during 5 min. with dry HCl and then with stirring at 0° with 10% excess iso-AmONO, and the mixture diluted after 1.5 h. with 250 cc. Et₂O gave III, decomposed at 180-5°. I (3 g.) in 150 cc. 85% H₃PO₄ treated with stirring at 0° slowly with concentrated aqueous NaNO₂ and then with saturated aqueous NaOAc yielded 3(5),3′(5′)-diazoaminopyrazole, C₆H₇N₇, yellowish crystals, decomposed at 186-7.5° (MeOH-NH₄OH). III (0.7 g.) in CHCl₃ adjusted at 0° with 50 cc. saturated aqueous Na₂CO₃ to pH 8, the aqueous phase extracted with CHCl₃, and the CHCl₃ solution evaporated cold in vacuo gave long needles of IV, which decomposed rapidly at room temperature with the formation of brown insoluble products. III (1 g.) in 150 cc. CHCl₃ treated at -10° with 3 cc. Et₃N gave a solution of IV. IV in solution treated carefully with CHCl₃ saturated with HCl yielded III. III (from 4 g. I) in a little H₂O treated at 0° with 7 g. NaI in 150 cc. H₂O, the mixture heated 0.5 h. on the water bath, evaporated in vacuo, and the residue extracted with Et₂O yielded 6% V, needles, m. 72-3° (H₂O). IV (from 1.2 g. I) in CHCl₃ treated at 0° with 4 g. 68% HI, the mixture warmed to room temperature, and worked up in the usual manner gave V. A solution of III (from 3.5 g. I added dropwise at 0° to 12.5 g. VI in 10% aqueous NaOH) gave 2.8 g. coupling product, C₁₃H₈N₄, yellow needles from much H₂O, yellow-red platelets from aqueous MeOH, m. 192-4°; the filtrate gave addnl. product. IV solution from III in CHCl₃ treated with concentrated VI in CHCl₃ and evaporated also gave the coupling product, yellow-red leaflets, m. 192-4° (aqueous MeOH). The UV and IR absorption spectra of III and IV were recorded.

Chemische Berichte published new progress about 3553-12-6. 3553-12-6 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Amine,Amide, name is 3-Acetamidopyrazole, and the molecular formula is C5H7N3O, Application In Synthesis of 3553-12-6.

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

Di Fabio, Romano published the artcileSynthesis and Pharmacological Characterization of Novel Druglike Corticotropin-Releasing Factor 1 Antagonists, Quality Control of 3553-12-6, the publication is Journal of Medicinal Chemistry (2008), 51(23), 7370-7379, database is CAplus and MEDLINE.

To identify new CRF₁ receptor antagonists, an attempt to modify the bis-heterocycle moiety present in the top region of the dihydropyrrole[2,3]pyridine template was made following new pharmacophoric hypothesis on the CRF₁ receptor antagonists binding pocket. In particular, the 2-thiazole ring, present in the previous series of compounds, was replaced by more hydrophilic non aromatic heterocycles able to make appropriate H-bond interactions with amino acid residues Thr192 and Tyr195. This exploration, followed by an accurate anal. of the substitution of the pendant aryl ring, enabled identification of in vitro potent compounds, e.g., I, showing excellent pharmacokinetics and outstanding in vivo activity in animal models of anxiety, both in rodents and primates.

Journal of Medicinal Chemistry published new progress about 3553-12-6. 3553-12-6 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Amine,Amide, name is 3-Acetamidopyrazole, and the molecular formula is C5H7N3O, Quality Control of 3553-12-6.

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

Dorgan, Roderick J. J. published the artcileN-Alkyl and N-acyl derivatives of 3(5)-aminopyrazole, Safety of 3-Acetamidopyrazole, the publication is Journal of Chemical Research, Synopses (1979), 198, database is CAplus.

3(5)-Aminopyrazole (I) underwent benzylation on the exocyclic N to give II [R = H, R¹ = R² = CH₂Ph; R = R¹ = H, R² = CH₂Ph (III)] whereas acetylation gave II (R = R¹ = Ac, R² = H), which on subsequent benzylation gave II (R = CH₂Ph, R¹ = Ac, R² = H) and IV (R = CH₂Ph, R¹ = H, R² = Ac) (V). In the presence of MeCOCH₂CO₂Et, III gave the pyrazolo[1,5-a]pyrimidine VI (R = CH₂Ph) which was debenzylated to VI (R = H). PhCH₂NHNH₂ reacted with CH₂:CClCN to give IV (R = CH₂Ph, R¹ = R² = H) which on acetylation gave V. I with phthalic anhydride gave II (R = H, NR¹R² = phthalimido) which on benzylation and benzyloxymethylation gave II (R = CH₂Ph, R¹R² as before) and IV (R = CH₂OCH₂Ph, R¹R² as before), resp.

Journal of Chemical Research, Synopses published new progress about 3553-12-6. 3553-12-6 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Amine,Amide, name is 3-Acetamidopyrazole, and the molecular formula is C5H7N3O, Safety of 3-Acetamidopyrazole.

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

Sandhu, Bhupinder published the artcileAssessment of computational tools for predicting supramolecular synthons, Quality Control of 3553-12-6, the publication is Chemistry (Basel, Switzerland) (2021), 3(2), 612-629, database is CAplus.

The ability to predict the most likely supramol. synthons in a crystalline solid is a valuable starting point for subsequently predicting the full crystal structure of a mol. with multiple competing mol. recognition sites. Energy and informatics-based prediction models based on mol. electrostatic potentials (MEPs), hydrogen-bond energies (HBE), hydrogen-bond propensity (HBP), and hydrogen-bond coordination (HBC) were applied to the crystal structures of twelve pyrazole-based mols. HBE, the most successful method, correctly predicted 100% of the exptl. observed primary intermol.-interactions, followed by HBP (87.5%), and HBC = MEPs (62.5%). A further HBC anal. suggested a risk of synthon crossover and synthon polymorphism in mols. with multiple binding sites. These easy-to-use models (based on just 2-D chem. structure) can offer a valuable risk assessment of potential formulation challenges.

Chemistry (Basel, Switzerland) published new progress about 3553-12-6. 3553-12-6 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Amine,Amide, name is 3-Acetamidopyrazole, and the molecular formula is C5H7N3O, Quality Control of 3553-12-6.

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

Sharma, Suresh Chandra published the artcileSynthesis, reactions, and nuclear magnetic resonance spectroscopy of 4-methyl-6H-pyrazolo(3,4-b)azepin-7-ones, Quality Control of 3553-12-6, the publication is Canadian Journal of Chemistry (1979), 57(23), 3034-40, database is CAplus.

I (R = H, Me, Ph, halogenated phenyl; R¹ = H, Me) reacted with Et levulinate to give II (same R, R¹) and acetamidopyrazoles. The courses of methylation and bromination of some II were examined; conversion of one pyrazoloazepinone to 7-chloropyrazoloazepine and amination gave 7-(substituted amino)pyrazoloazepines. Structural assignments, tautomeric preferences, and through-space interactions between substituents were established through NMR (¹H and ¹³C). Some II exhibit significant antiinflammatory and analgesic effects in mice.

Canadian Journal of Chemistry published new progress about 3553-12-6. 3553-12-6 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Amine,Amide, name is 3-Acetamidopyrazole, and the molecular formula is C10H11N3O3S, Quality Control of 3553-12-6.

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