Tag: M.W:200-300

Related Products of 1150271-23-0, These common heterocyclic compound, 1150271-23-0, name is tert-Butyl 4-bromo-1H-pyrazole-1-carboxylate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

In the reaction kettle, adding tetrahydrofuran 4.5 kg and 1 – BOC – 4 – brompyrazole (2.01 kg, 9.2 muM), stirring 0.5 hours, cooling to -20 C, maintain -10 C -0 C dropwise 3.2molBu3MgLi [preparation method: 1.0eq butyl magnesium chloride in -10 C -0 C lower drop by adding 2.0 equivalent butyl lithium in], TLC detection reaction, maintain the exchange completion -10 C -0 C dropwise dimethylamine fundamental frequency that mellow boron ester (1.61 kg, 9.4 muM) dissolved in 1 kg of the mixed solution in tetrahydrofuran, the completion of the dropping, thermal insulation 2 hours, natural heating stirring overnight. The control temperature of not more than 30 C after adding glacial acetic acid, after detecting the protecting group removal, stop stirring filtration, the mother liquor recovered, solid add triethylamine (1.01 kg, 10 muM) and ethyl acetate 8 kg after, heating to reflux reaction, the proportion of internal standard detecting product is not increased when, after lowering the filtering, the filtrate obtained after the distillation is a kind of white solid, by adding heptane cooling to 0 C beating, filtering, 50 – 60 C vacuum drying to obtain white solid pyrazole -4 – boric acid frequency that alcohol ester 1.36 kg, GC: 99.1%, HNMR consistent with the literature value, yield 76%.

The synthetic route of 1150271-23-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cangzhou Puri Oriental Technology Co., Ltd; Leng, Yanguo; Gui, Qian; Shen, Haibing; (5 pag.)CN106188116; (2016); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 294877-29-5, name is 1-(3-Bromophenyl)-3,5-dimethyl-1H-pyrazole, belongs to pyrazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 294877-29-5, HPLC of Formula: C11H11BrN2

In another step, 2-[3-(3,5-Dimethylpyrazol-1-yl)-phenoxy]-N-(tetrahydropyranyl)carbazole was synthesized. To a 100 mL sealed tube was added with N-tetrahydropyranyl-2-hydroxycarbazole (880 mg, 3.0 mmol), N-(3-Bromophenyl)-3,5-dimethylpyrazole (826 mg, 3.30 mmol), Cesium carbonate (2.9 g, 3 mmol), copper(I) iodide (57 mg, 0.3 mmol), N,N-dimethylglycine (93 mg, 0.9 mmol) and 1,4-dioxane (8 mL) in glove box, and the mixture was stirred at 90 C. for 3 days. After cooling to rt, the mixture was treated with water (75 mL) and ethyl acetate (40 mL), and the water phase was extracted with ethyl acetate (3×30 mL). The organic extracted phase was combined, washed with brine (3×30 mL), dried with magnesium sulfate and concentrated. The resulting crude product was purified with an silica gel chromatography with hexane/ethyl acetate=3:1 as eluent to give an white colloidal solid. (1.12 g, 79% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(3-Bromophenyl)-3,5-dimethyl-1H-pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; Li, Jian; Turner, Eric; Hang, Xiaochun; US2012/215001; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1280210-79-8, A common heterocyclic compound, 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, molecular formula is C10H15N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Under N2 protection and a condition free of water and oxygen, Intermediate 2 (604 mg, 2.87 mmol) wasdissolved in tetrahydrofuran (20 ml), which was cooled to 0C, and sodium hydride (180 mg, 60 wt%, 4.5 mmol) wasadded, followed by stirring for 30 min. Cyclopropylsulfonyl chloride (1.27 g, 9.0 mmol) was added dropwise, and thetemperature was allowed to rise spontaneously to room temperature, followed by reaction for 1 hour. The reaction was quenched by addition of water (20 ml) to the reaction solution, which was then extracted with ethyl acetate (20 ml32).The organic phases were combined, dried over anhydrous sodium sulfate, concentrated, re-dissolved in 5 ml tetrahydrofuran,and cooled to -10C to 0C. Potassium t-butoxide (36 mg, 0.32 mmol) was added, and the reaction was allowedto proceed for 28 hours at this temperature. After the reaction was completed, an aqueous solution of citric acid (1 ml,15%) was added, and water (10 ml) was added. The solution was extracted with ethyl acetate (20 mL33). The organicphases were combined, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gelcolumn chromatography (petroleum ether/ethyl acetate (v/v) = 2:1) to obtain a white solid 1a (660 mg, yield 73%).

The synthetic route of 1280210-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan Haisco Pharmaceutical Co., Ltd.; ZHANG, Chen; WANG, Jianmin; LI, Caihu; WEI, Yonggang; (64 pag.)EP3159344; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1227611-94-0,Some common heterocyclic compound, 1227611-94-0, name is 4-(4-Iodo-1H-pyrazol-1-yl)cyclohexanone, molecular formula is C9H11IN2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 89: 4-(4-{3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5- yl}-pyrazol-1-yl)cyclohexanone[428] A 20 ml sealable vial was charged with 3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-5- (4,4,5,5-tetramethyl[1 ,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (80.0 mg, 0.156 mmol), 4-(4-lodopyrazol-1-yl)cyclohexanone (52.5 mg, 0.172 mmol), Pd(PPh3)4 (12.0 mg, 0.0103 mmol), potassium carbonate (71.8 mg, 0.514 mmol), and 4:1 dioxane:water (5 mL). The cap was sealed and the vial was evacuated and backfilled with nitrogen (3x). After that, the vial was heated at 90 C for 2 h. The reaction mixture was partitioned between EtOAc/H2O (15 ml/10 ml). The aqueous phase was extracted with EtOAc (10 ml). The combined organic extracts were washed with water (10 ml) and brine (10 ml), dried over MgSO4, filtered, and concentrated in vacuo to give a brown oil that was purified by prep. TLC eluting with 4% MeOH/DCM to give the title compound. 1H NMR (400 MHz, CDCI3 ): delta = 1.88 (d, J = 7.2 Hz, 3 H), 2.31-2.68 (m, 8 H), 4.64 (tt, J = 1 1.8, 4.0 Hz, 1 H), 5.28 (q, J = 7.2 Hz, 1 H), 7.01 (dd, J = 8.0 & 8.8 Hz, 1 H), 7.30 (s, 1 H), 7.32 (brs, 1 H), 7.48 (s, 1 H), 7.60 (d, J = 0.8 Hz, 1 H), 7.66 (d, J = 0.8 Hz, 1 H), 8.41 (brs, 1 H), 9.77 (brs, 1 H). MS(ES+): m/z = 471.16/473.11 (100/68) [MH+]. HPLC: tR = 3.39 min (polar_5 min, ZQ3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(4-Iodo-1H-pyrazol-1-yl)cyclohexanone, its application will become more common.

Reference:
Patent; OSI PHARMACEUTICALS, INC.; CHEN, Xin; JIN, Meizhong; KLEINBERG, Andrew; LI, An-hu; MULVIHILL, Mark, J.; STEINIG, Arno, G.; WANG, Jing; WO2010/59771; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1202993-11-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1202993-11-0, name is 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Synthesis of 5-chloro-3-(difluoromethyl)-l-methyl-lH-pyrazole-4-carbonyl chloride (example Vc-1); 3.2 g of 5-chloro-3-(difluoromethyl)-l-methyl-lH-pyrazole-4-carboxylic acid and 44.3 ml of thionyl chloride were refluxed for 5 hours. After cooling down, the reaction mixture was evaporated under vacuum to yield 3.5 g of 5-chloro-3-(difluoromethyl)-l-methyl-lH-pyrazole-4-carbonyl chloride as a yellow oil.¾ NMR (400 MHz, CHC13- 6) delta ppm : 3.97 (s, 3H); 7.00 (t, J= 52.01 Hz, 1 H); IR (TQ) : 1759 and 1725 om C=0);

The synthetic route of 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CROPSCIENCE AG; GREUL, Joerg; BENTING, Juergen; DAHMEN, Peter; WACHENDORFF-NEUMANN, Ulrike; WO2012/65932; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. SDS of cas: 39806-90-1

General procedure: 4-Iodo-1-methyl-1H-pyrazole 1 (101 mg, 0.5 mmol) and phenylboronic 2 (59 mg, 0.5 mmol) were dissolved in DME (3 mL) and H2O (1.2 mL) in a microwave vial under a nitrogen atmosphere. Pd(PPh3)4 (2 mmol%, 11.6 mg) and Cs2CO3 (407.3 mg, 1.25 mmol) were added, and the reaction mixture was irradiated in a microwave apparatus at 90 C for 5-12 min. After the reaction mixture was cooled to ambient temperature, the product was concentrated, and the crude mixture was purified by silica gel column chromatography using petroleum ether/acetone as eluent to give the title compound.

The synthetic route of 4-Iodo-1-methyl-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cheng, Hua; Wu, Qiong-You; Han, Fan; Yang, Guang-Fu; Chinese Chemical Letters; vol. 25; 5; (2014); p. 705 – 709;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 330792-70-6, name is 3-Amino-5-(4-phenoxyphenyl)pyrazole-4-carbonitrile, belongs to pyrazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 330792-70-6, COA of Formula: C16H12N4O

To a solution of tert-butyl 3 -(tosyloxy)piperidine- 1 -carboxylate (355 mg, 1.0 mmol) and 5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile (276 mg, 1.0 mmol) in 5 mL of DIVIF is added Cs2CO3 (650 mg, 2.0 mmol). A tosyloxy leaving group is employed in this reaction. The mixture is stirred at RT for 16 hours, 75 C for 3 hours and 60 C for 16 hours. The mixture is concentrated washed with brine (100 mL x 3) and dried over Na2504. The material is concentrated and purified by chromatography column on silica gel (eluted with petroleum ether/ethyl actate = 3/1) to afford 60 mg (13%) of tert-butyl 3-(5-amino-4-cyano-3-(4- phenoxyphenyl)- 1H-pyrazol- 1 -yl)piperidine- 1 -carboxylate as a yellow oil.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-Amino-5-(4-phenoxyphenyl)pyrazole-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACERTA PHARMA B.V.; ROTHBAUM, Wayne; LANNUTTI, Brian; (349 pag.)WO2017/46747; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1029413-51-1,Some common heterocyclic compound, 1029413-51-1, name is 4-Amino-1-(1-boc-azetidin-3-yl)-1H-pyrazole, molecular formula is C11H18N4O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 14: Synthesis of I -(2-(2-(2-((I -(azetidin-3-yl)-I H-pyrazol-4-yl)amino)-5- chloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide (14)H2N.O H2NO_ H1BoC_NN/j NH2 + CI N1>A14 A18HNNNY(a) tert-Butyl 3-(4-((4-(2-(1-carbamoylcyclopropyl)phenethyl) -5-chloropyrimidin-2-yI)amino)- 1H-pyrazol- 1-yI)azetidine- 1-carboxylate (A 18) A suspension of 1-(2-(2-(2,5-dichloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide A14 (0.100 g, 0.297 mmol), 052003 (0.291 g, 0.892 mmol) and tert-butyl 3-(4-amino-1H-pyrazol-1-yl)azetidine-1-carboxylate (0.142 g, 0.595 mmol) in dioxane (3 mL) was sonicated for 10 minutes. Xantphos(6.9 mg, 12 pmol) and Pd(ll) acetate (1.3 mg, 5.9 pmol) were added to thesuspension and the mixture was irradiated in the microwave for 20 minutes at 120 00 The resulting mixture was adsorbed onto silica gel and purified by columnchromatography (Biotage Isolera, 24 g Si02 cartridge, 0-100% EtOAc in petroleum benzine 40-60 00 then 0-40% MeOH in EtOAc) to give the title compound A18 as ayellow oil (110 mg, 69%). LCMS-A: rt 6.349 mm; m/z 538.3 [M+H].

The synthetic route of 1029413-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LIMITED; FOITZIK, Richard Charles; MORROW, Benjamin Joseph; HEMLEY, Catherine Fae; LUNNISS, Gillian Elizabeth; CAMERINO, Michelle Ang; GANAME, Danny; STUPPLE, Paul Anthony; LESSENE, Romina; KERSTEN, Wilhelmus Johannes Antonius; HARVEY, Andrew John; HOLMES, Ian Peter; WO2014/26243; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 39806-90-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-iodo-1-methyl-IH-pyrazole (55 gm, 0.264 moles) in N,Ndimethylacetamide (100 ml), potassium ferrocyanide (24.5 gm, 0.058 moles), palladium (II) acetate (0.592 gm, 0.0026 moles)and sodium carbonate (27.98 gm, 0.264 moles) wereadded. The reaction mixture was evacuated and backfihled with nitrogen (3 times). The mixture was stirred for 12 hour at 100-1 10C. Progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 20-30C, to this added Dl water (500 ml), ethyl acetate (500 ml) and stirred for 1 hour at 20-30C. The reaction mixture was filtered through pad of celite. The organic layer was separated and aqueous layer was extracted withethyl acetate (200 ml), stirred for 15 mm and separated the final aqueous layer and organic layer. The organic layer was washed with brine solution (200 ml). Ethyl acetate was recovered at reduced pressure at 60-70C. The mixture was degassed for 2 hour at reduced pressure at 60-70C, cooled the mixture to 20-30C: Hexane (400 ml) was added to the mixture and stirred for 1 hour at 20-30C. The solid product obtained was filtered, washedwith cold Dl water (100 ml) and dried at 40-50C to afford the product, I-Methyl-IHpyrazole-4-carbonitrile.Drywt : 17.94gmYield : 0.32 w/w (63%);

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Iodo-1-methyl-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RALLIS INDIA LIMITED; PALIMKAR, Sanjay Sambhajirao; PAWAR, Jivan Dhanraj; SANKAR, B; KADAM, Subhash Rajaram; HINDUPUR, Rama Mohan; PRABHU, Venkatesh M.; PATI, Hari Narayan; SUPHALA, Vadiraj Gopinath; MANE, Avinash Sheshrao; WO2014/2109; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 345637-71-0, name is 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 345637-71-0

To a solution of (5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acid (9.1 g, 36.1 mmol) in DMF (100 mL) is added diisopropylethylamine (45 mL, 216 mmol), followed by O- (benzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium tetrafluoroborate (15.5 g, 39.7 mmol). After stirring 15 min at RT, 2-piperidin-4-yl-thiazole-4-carboxylic acid ethyl ester hydrochloride (10 g, 36.1 mmol) is added to the reaction mixture. After stirring overnight at RT, solvent is evaporated and the resulting yellow oil is dissolved in ethylacetate (300 mL), washed with saturated aqueous sodium bicarbonate solution (300 mL), 1 M HCI solution (300 mL), and brine (100 mL). The organic layer is dried over sodium sulfate, filtered, and evaporated under reduced pressure. The crude mixture is purified by column chromatography on silica gel (dichloromethane/methanol 10: 1) to give 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)- acetyl]-piperidin-4-yl}-thiazole-4-carboxylic acid ethyl ester (13.6 g, 88 %). 1 H-NMR (400 – -MHz, CDCI3): delta = 1.40 (t, 3H), 1.70-1.85 (m, 2H), 2.16-2.30 (m, 2H), 2.32 (s, 3H), 2.79-2.89 (m, 1 H), 3.22-3.43 (m, 1 H), 4.03-4.12 (m, 1 H), 4.42 (q, 3H), 4.54-4.69 (m, 1 H), 4.93-5.08 (2d, 2H (diastereotopic)), 6.35 (s, 1 H), 8.10 (br, 1 H). MS: m/z = 209 (M+1).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 345637-71-0.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SULZER-MOSS, Sarah; LAMBERTH, Clemens; RESPONDEK, Mathias, Stephan; QUARANTA, Laura; CEDERBAUM, Fredrik; BERTHON, Guillaume; WO2012/69633; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics