33641-15-5Relevant academic research and scientific papers
Method for preparing 1-methyl-5-hydroxypyrazole by using microchannel reactor
-
Paragraph 0027-0048, (2021/06/22)
The invention relates to a method for preparing 1-methyl-5-hydroxypyrazole by using a microchannel reactor, and belongs to the technical field of fine chemical engineering. According to the invention, methyl 3-methoxyacrylate and a methylhydrazine aqueous solution are used as reaction raw materials, and the microchannel reactor is used as reaction equipment to prepare 1-methyl-5-hydroxypyrazole. Compared with a kettle type reaction, the yield and the reaction purity are obviously improved. In addition, no solvent is used in the preparation process, so that few hazardous wastes are generated. The microchannel reactor is used for preparing the 1-methyl-5-hydroxypyrazole, continuous production can be achieved, the operation process is simplified, and the production efficiency and safety are improved.
Preparation method of pyrazole type herbicide intermediate 1-methyl-5-hydroxypyrazole
-
Paragraph 0035; 0038-0040; 0043-0045; 0048-0049, (2021/03/31)
The invention belongs to the technical field of preparation of pyrazole type herbicide intermediates, and particularly relates to a preparation method of a pyrazole type herbicide intermediate 1-methyl-5-hydroxypyrazole. The preparation method of the 1-methyl-5-hydroxypyrazole comprises the following steps: (1) in the presence of alkali, enabling dimethyl malonate of a compound (1) to react with aformamide compound and an alkylation reagent in a solvent to generate a compound (2); and (2) carrying out cyclization reaction on the obtained compound (2) and methylhydrazine/hydrazine hydrate in asolvent, and carrying out hydrolysis and decarboxylation by using an acid to obtain a compound (3). According to the method, DMF, an alkylation reagent and the compound (1) react to obtain the compound (2), the obtained compound (2) is good in selectivity when being subjected to ring-closure reaction with methylhydrazine (or hydrazine hydrate), and a target product compound (3) with higher yieldand purity can be obtained. Moreover, the raw materials used in the synthesis method disclosed by the invention are relatively weak in corrosivity, easy to recover and relatively low in price, so thatindustrial production is facilitated.
Synthesis method of 1-methyl-5-hydroxy pyrazole
-
Paragraph 0014; 0030-0046, (2021/03/13)
The invention relates to a synthesis method of 1-methyl-5-hydroxy pyrazole, which comprises the following steps of dropwisely adding tetrahydropyrrole into diethyl ethoxymethylene malonate at room temperature, and reacting at 15-80 DEG C for 2-6 hours to obtain a reaction solution A containing a compound represented by a formula (II), dropwise adding a methylhydrazine aqueous solution into the reaction solution A, and reacting at 15-80 DEG C for 2-6 hours to obtain a reaction solution B containing a compound shown as a formula (III), dropwise adding an acidic solution into the reaction solution B, and heating and refluxing for 4-8 hours at 90-120 DEG C after dropwise adding to obtain a reaction solution C containing a compound shown as a formula (IV), and carrying out post-treatment on thereaction solution C to obtain the target compound 1-methyl-5-hydroxy pyrazole. The synthesis method has the advantages of higher activity, higher reaction rate, better selectivity, higher total yield, cheap and accessible raw materials and simple post-treatment, and can obtain the solid 1-methyl-5-hydroxy pyrazole with higher purity.
Synthesis method and application of topramezone impurity
-
Paragraph 0020; 0028, (2019/10/01)
The invention discloses a synthesis method of topramezone impurity. The method includes: taking 2, 3-dimethylaniline as the starting raw material, carrying out methyl sulfidation, bromination, oxidation, oximation and chlorination ring-closing to synthesize 3-[3-bromo-2-methyl-6-(methylsulfonyl)phenyl]-4, 5-dihydroisoxazole, and carrying out condensation with 1-methyl-5-hydroxypyrazole under an alkaline condition to synthesize 3-[2-methyl-3-(1-methyl-1H-pyrazole-5-oxyl)-6-(methylsulfonyl)phenyl]-4, 5-dihydroisoxazole. The invention also discloses application of the corresponding product. The synthesis method provided by the invention has the characteristics of simple operation, easily control process, and a product yield of 40%-80%. The obtained product can be used as a standard substancefor detecting and monitoring the synthesis of topramezone.
Flexible analogues of WAY-267,464: Synthesis and pharmacology at the human oxytocin and vasopressin 1a receptors
Jorgensen, William T.,Gulliver, Damien W.,Werry, Eryn L.,Reekie, Tristan,Connor, Mark,Kassiou, Michael
, p. 730 - 740 (2016/01/09)
A previously identified, non-peptidic oxytocin (OT) receptor agonist WAY-267,464 (1) and nine novel derivatives (3, 4a-7a, 4b-7b) were synthesised and evaluated in vitro with the aim of systematically exploring hydrogen bonding interactions and ligand flexibility. All analogues were subjected to competition radioligand binding assays at human oxytocin (OT) and arginine vasopressin 1a (V1a) receptors. Physiological activity was determined using whole cell IP1 accumulation assays. Under these conditions, WAY-267,464 had higher affinity for the V1a receptor compared to the OT receptor (8.5x more selective) with poor functional selectivity (2x selective for OT receptor agonism over V1a receptor antagonism). Methylation of the resorcinol moiety (3) reversed the OT receptor pharmacological profile, removing agonist activity and inducing antagonist activity, without altering V1a receptor pharmacology. All flexible tethered derivatives removed OT receptor affinity and activity resulting in the generation of highly selective V1a receptor ligands.
Pyrazole ketone compound or its salt, preparation method thereof, and use of the herbicide composition (by machine translation)
-
Paragraph 0063; 006=5, (2016/10/08)
This application pertains to the field of agricultural chemicals, in particular to a pyrazole ketone compound or its salt, preparation method, herbicidal composition and use. The ketone compounds states the pyrazole shown as formula I: In the formula, R 1 R 2 N representative containing substituted or unsubstituted 1-3 of the aza-3-8-membered nitrogen-containing heterocyclic base; or R 1, R 2 respectively represents hydrogen, C 1-8 alkyl etc.; R 3 representative hydrogen, C 1-4 alkyl, alkenyl, alkynyl, or unsubstituted C 1-4 alkyl substituted C 3-6 cycloalkyl; R 4 represents methyl, ethyl, n-propyl, isopropyl, cyclopropyl; X represents hydrogen, -S (O) n R 6, -R 7, containing substituted or unsubstituted 1-4 of the aza-3-8-membered heterocyclic group, wherein n representative 1, 2, 3, R 6 represents a substituted or unsubstituted alkyl or aryl, R 7 represents a substituted or unsubstituted alkyl, aryl, alkanoyl or sweet-smelling acyl. The present invention provides good efficacy of the pharmaceutical actives, easy to use, low cost, has good commercial value. (by machine translation)
Pyrazolo[1,4]diazepines as non-peptidic probes of the oxytocin and vasopressin receptors
Reekie, Tristan A.,McGregor, Iain S.,Kassiou, Michael
supporting information, p. 4568 - 4571 (2015/01/09)
An improved synthesis of differently substituted pyrazolo[1,4]diazepine compounds is reported. In addition, we have used this methodology to obtain non-peptidic compounds to probe the oxytocin and vasopressin receptors.
PYRAZOLE DERIVATIVES AS 5-LO INHIBITORS
-
Page/Page column 130; 141, (2009/07/03)
The invention relates to compounds of formula (I) processes for their preparation, their use as 5-lipoxygenase inhibitors and pharmaceutical compositions containing the same.
SUBSTITUTED BICYCLOCARBOXYAMIDE COMPOUNDS
-
Page/Page column 49, (2008/12/05)
This invention provides a compound of the formula (I). These compounds are useful for the treatment of disease conditions caused by overactivation of the VR1 receptor such as pain, or the like in mammal. This invention also provides a pharmaceutical composition comprising the above compound.
Method for producing 1-substituted 5-Hydroxypyrazoles
-
, (2008/06/13)
The invention relates to a process for preparing 1-substituted 5- and/or 3-hydroxypyrazoles of the formulae I and II in which R1 is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl or C1-C4-alkoxy, where these groups may be substituted by halogen, C1-C4-alkoxy, phenoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthiocarbonyl or by a cyclic ring system having 3-14 ring atoms, which comprises reactingan alkyl 3-alkoxyacrylate of the formula III in which R2, R3 independently of one another are C1-C6-alkyl or C3-C6-cycloalkyl with a hydrazine of the formula IV in which R1 is as defined abovea) at a pH of 6-11 to give 5-hydroxypyrazoles of the formula I orb) at a pH of 11-14 to give 3-hydroxypyrazoles of the formula II.
