Tag: M.W:200-300

Related Products of 866837-96-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 866837-96-9 name is Ethyl 5-amino-1-phenyl-1H-pyrazole-3-carboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Pyridine (12.9 mL, 161 mmol) was added to a solution of ethyl 5-amino-1-phenyl-1H- pyrazole-3-carboxylate (9.32 g, 40.3 mmol) and 5-bromo-2-chlorobenzoic acid (10.4 g,44.3 mmol) in 2-methyl-tetrahydrofuran (100 mL). The reaction was heated to 85C before the addition of propylphosphonic anhydride (38.5 mL, 60.4 mmol, 50% solution in EtOAc) drop-wise. The reaction was heated at 85C for 16 hours before cooling to room temperature. The organic solution was washed with saturated aqueous sodium hydrogen carbonate solution (3 x 25 mL), saturated brine (30 mL) and concentrated invacuo. The resulting solid was triturated with TBME (5 x 50 mL) to afford the titlecompound (13.7 g, 76%).1H NMR (400MHz, CDCI3): O ppm 1.42 (t, 3H), 4.44 (q, 2H), 7.25 (d, 1H), 7.39 (5, 1H),7.51 (m, 5H), 8.02 (d, 1H), 8.43 (5, 1H).LCMS Rt = 3.13 minutes MS mlz 448 [M+H]

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

Reference:
Patent; PFIZER INC.; BAGAL, Sharanjeet Kaur; CUI, Jingrong Jean; GREASLEY, Samantha Elizabeth; LUNNEY, Elizabeth Ann; MCALPINE, Indrawan James; NAGATA, Asako; NINKOVIC, Sacha; OMOTO, Kiyoyuki; SKERRATT, Sarah Elizabeth; STORER, Robert Ian; WARMUS, Joseph Scott; WO2015/170218; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 285984-25-0,Some common heterocyclic compound, 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, molecular formula is C14H19N3, 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.

To a stirred solution of CDI (223 mg, 1 .38 mmol) in dry DCM (3.5 mL) was added Intermediate A1 (315 mg, 1 .38 mmol) as a solid, portion-wise, over 12 min and the resulting solution maintained at RT for 4 hr. An aliquot of this solution (2.0 mL, 0.79 mmol) was added to a solution of Intermediate G1 , (140 mg, 0.39 mmol) in dry THF (5.0 mL), and the reaction mixture was kept at RT for 17 hr and was then partitioned between saturated aq. NaHC03 (30 mL) and DCM (30 mL). The aq. layer was extracted with DCM (30 mL) and the combined organic extracts were dried and evaporated in vacuo. The residue was purified by flash column chromatography (Si02, 12 g, [5% MeOH in EtOAc] in isohexane, 0-45%, gradient elution) to afford the title compound, Example 14, as an off white solid (127 mg, 52%); R’ 5.40 min (Method 1 basic); m/z 61 1/613 (M+H)+ (ES+); 1H NMR (400 MHz, DMSO-d6) delta: 1 .26 (9H, s), 2.37 (3H, s), 3.37 (3H, s), 4.07 (2H, s), 5.31 (2H, s), 6.34 (1 H, s), 7.18-7.23 (2H, overlapping m), 7.31 -7.34 (2H, overlapping m), 7.38-7.40 (2H, overlapping m), 7.85 (1 H, d), 8.21 (1 H, br s), 8.33 (1 H, dd), 8.60 (1 H, br s), 8.95 (1 H, br s), 10.01 (1 H, br s).

The synthetic route of 285984-25-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RESPIVERT LIMITED; KING-UNDERWOOD, John; HARDY, George; MURRAY, Peter John; WILLIAMS, Jonathan Gareth; ONIONS, Stuart Thomas; WO2011/121366; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, 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 285984-25-0, category: pyrazoles-derivatives

To a solution of CDI (510 mg, 3.15 mmol) in dry DCM (6.0 mL) at RT was added Intermediate A1 (722 mg, 3.15 mmol) portionwise over 15 min and the reaction mixture maintained at RT for 20 hr. An aliquot of the resulting solution (840 mu, 0.44 mmol) was added to a solution of Intermediate M1 , (81 mg, 0.21 mmol) in dry DCM (4.0 mL) and the reaction mixture was maintained at RT for 1 day and was then partitioned between saturated aq. NaHC03 (20 mL) and DCM (20 mL). The aq layer was separated and extracted with DCM (20 mL) and the combined organic extracts were dried and evaporated in vacuo. The residue was purified by flash column chromatography (Si02, 12 g, [1 % NH3 in MeOH] in DCM, 0-10%, gradient elution) to provide the title compound, Example 24, as a white solid (53 mg, 37 %); Rl 5.39 min (Method 1 basic); m/z 640/642 (M+H)+, (ES+); 1H NMR (400 MHz, DMSO-de) delta: 1.27 (9H, s), 2.16 (6H, s), 2.33 (2H, t), 2.34 (3H, s), 3.21 (2H, td), 6.38 (1 H, s), 7.23-7.28 (2H, overlapping m), 7.33-7.37 (3H, overlapping m), 7.41 (2H, m), 8.08 (1 H, d), 8.35 (1 H, d), 8.83 (1 H, br s), 9.17 (1 H, br s), 9.68 (1 H, br s).

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-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RESPIVERT LIMITED; KING-UNDERWOOD, John; HARDY, George; MURRAY, Peter John; WILLIAMS, Jonathan Gareth; ONIONS, Stuart Thomas; WO2011/121366; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 500011-84-7, These common heterocyclic compound, 500011-84-7, name is 3-Bromo-1-(dimethylsulfamoyl)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.

Step 3: Preparation of 3-bromo-lff-pyrazole; To 3-bromo-pyrazole-l-sulfonic acid dimethylamide (21.3 g) was slowly added trifluoroacetic acid (30 mL) and stirred at room temperature for 2 h. Hexane was added and the formed precipitate was filtered off and washed with hexane. The filtrate was diluted with MTB-ether, washed with sat. NaHC03-solution, water and brine, dried over MgSO4 and concentrated in vacuum to afford 10.7 g of a colorless oil containing 80% of the title compound of the formulaBrH The residue was used for the next step without further purification .1H-NMR (CDCl3, TMS) 8 (ppm) : 6.37 (IH, d, J = 3 Hz), 7.55 (IH, d, J = 3 Hz), 12.6 (IH, br s).

The synthetic route of 500011-84-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2008/130021; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 179692-08-1, name is Ethyl 4-iodo-1H-pyrazole-5-carboxylate, molecular formula is C6H7IN2O2, 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. Recommanded Product: Ethyl 4-iodo-1H-pyrazole-5-carboxylate

At 0C, NaH (902.12 mg, 22.55 mmol, 60%) was added portionwise into a solution of Example 1A (5 g, 18.79 mmol) in DMF (30 mL) and stirred for 30 min. A solution of dibromodifluoromethane (9.00 g, 42.89 mmol) in DMF (30 mL) was added and stirred at 20C for 16 h. The reaction solution was quenched with water (100 mL) and extracted with ethyl acetate (50 mL * 3). The combined organic phase was washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered and evaporated to give a residue. The residue was purified by column chromatography to give the title compound as a brown liquid (2 g, 26.95%). 1H NMR (400 MHz, CHLOROFORM-d) delta=8.00 (s, 1H), 4.48 (q, J=7.3 Hz, 2H), 1.45 (t, J=7.2 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 179692-08-1, its application will become more common.

Reference:
Patent; Chai Tai Tianqing Pharmaceutical Group Co., Ltd.; Medshine Discovery Inc.; LIU, Shilan; WANG, Dahai; LIANG, Guibai; HU, Guoping; LI, Jian; CHEN, Shuhui; (167 pag.)EP3418282; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate, 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 37687-24-4, Recommanded Product: 37687-24-4

In 250 mL of acetonitrile was dissolved 2-chloro-1-(i-methyl-1H- pyrazol-4-yl)ethanone (18.3 g, 115 mmol) and diethyl iH-pyrazole-3,5-dicarboxylate (24.5 g, 115 mmol) before finely ground K2C03 (31.9 g, 231 mmol) was added in one portion. The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was filtered and the cake was washed with acetonitrile (100 mL). The filtrate was concentrated in vacuo to a thick oil. The oil was dissolved in EtOAc (80 mL), and heptane (200 mL) was added slowly with stirring. The resultant solids were stirred for 2 hours, then filtered and washed with heptane. The solids were dried in a vacuum oven to afford diethyl 1-(2-(i-methyl-1H-pyrazol-4- yl)-2-oxoethyl)-1H-pyrazole-3,5-dicarboxylate (26.4 g, 77.4 mmol, 67.1 % yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Diethyl 3,5-pyrazoledicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ARRAY BIOPHARMA INC.; CELGENE CORPORATION; ALLEN, Shelley; BOYS, Mark Laurence; CHICARELLI, Mark J.; FELL, Jay Bradford; FISCHER, John P.; GAUDINO, John; HICKEN, Erik James; HINKLIN, Ronald Jay; KRASER, Christopher F.; LAIRD, Ellen; ROBINSON, John E.; TANG, Tony P.; BURGESS, Laurence E.; RIEGER, Robert Andrew; PHENEGER, Jed; SATOH, Yoshitaka; LEFTHERIS, Katerina; RAHEJA, Raj K.; BENNETT, Brydon L.; (223 pag.)WO2016/90285; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 92525-10-5, The chemical industry reduces the impact on the environment during synthesis 92525-10-5, name is 3-Iodo-1-methyl-1H-pyrazole, I believe this compound will play a more active role in future production and life.

Step 1-Synthesis of 2-(1-methyl-1H-pyrazol-3-yl)-4-(trimethylsilyl)but-3-yn-2-ol To a solution of 3-iodo-1-methyl-1H-pyrazole (378 mg, 1.82 mmol) in dry DCM (15 mL) at 0 C. under an atmosphere of nitrogen, was introduced ethylmagnesium bromide (2.0 mL of a 1.0M solution in THF, 2.0 mmol). After 30 minutes at 0 C., the reaction mixture was warmed to RT for 15 minutes, then introduced to a solution of 4-(trimethylsilyl)but-3-yn-2-one (0.37 ml, 2.18 mmol) in dry DCM (5 ml) at 0 C. under an atmosphere of nitrogen. The reaction mixture was warmed to RT for 16 hr. Following addition of saturated aqueous ammonium chloride (5 ml), the reaction mixture was extracted with DCM (3*5 mL extractions). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by silica gel flash column chromatography (heptane/EtOAc gradient) furnished the title compound as an orange-brown oil: 1H NMR (500 MHz, CDCl3) delta 0.15 (9H, d, J=3.5 Hz), 1.82 (3H, s), 3.18 (1H, s), 3.86 (3H, s), 6.28 (1H, d, J=2.2 Hz), 7.26 (1H, d, J=2.2 Hz); LC-MS: m/z=+222.95 (M+H)+.

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-Iodo-1-methyl-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Genentech, Inc.; US2012/214762; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 500011-84-7 as follows. category: pyrazoles-derivatives

To trifluoroacetic acid (70 mL) was slowly added [3-BROMO N, N DIMETHYL-1H] [PYRAZOLE-L-SULFONAMIDE] (i. e. the bromopyrazole product of Step B) (57.04 g). The reaction mixture was stirred at room temperature for 30 minutes and then concentrated at reduced pressure. The residue was taken up in hexane, insoluble solids were filtered off, and the hexane was evaporated to afford the crude product as an oil. The crude product was further purified by chromatography on silica gel using ethyl acetate/dichloromethane (10: 90) as eluent to afford an oil. The oil was taken up in dichloromethane, neutralized with aqueous sodium bicarbonate solution, extracted with dichloromethane [(3X),] dried over magnesium sulfate and concentrated to afford the title product as a white solid (25.9 g), m. p. [61-64 C.] 1H NMR (CDC13) 8 6.37 (d, 1H), 7.59 (d, 1H), 12.4 (br s, 1H).

According to the analysis of related databases, 500011-84-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; E.I. DU PONT DE NEMOURS AND COMPANY; WO2004/11447; (2004); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 51516-70-2 as follows. Application In Synthesis of 5-Amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile

General procedure: To a stirred solution of the intermediate compounds 1a-1d (1 mmol) and triethylamine (2 mmol) in DMF (12 mL) medium, a mixture of EDCI (1 mmol) and HOBt (1mmol) was added and the reaction mixture was stirred at room temperature for 30 min, then a mixture of compounds 2a-2d (1 mmol) and DMF (5 mL) was added, the reaction was stirred at room temperature. And the reaction progress was monitored by TLC. After completion of the reaction, the product was added into chloroform, then extracted from chloroform with water, and washed successively with 0.2 mol/L hydrochloric acid, water,2 mol/L sodium hydroxide, water, saturated sodium chloride, then dried, concentrated and purified by preparative thin layer chromatography (PE:EA = 8:1) followed by recrystallization from ethanol.

According to the analysis of related databases, 51516-70-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Xiao, Jin-Jing; Liao, Min; Chu, Ming-Jie; Ren, Zi-Li; Zhang, Xin; Lv, Xian-Hai; Cao, Hai-Qun; Molecules; vol. 20; 1; (2015); p. 807 – 821;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

179692-08-1, name is Ethyl 4-iodo-1H-pyrazole-5-carboxylate, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of Ethyl 4-iodo-1H-pyrazole-5-carboxylate

Example 15, Step C [00154] To a solution of compound 15c (38 g, 143 mmol) in acetonitrile (380 mL) at r.t. was added K2C03 (39.5 g, 286 mmol) and then PMBCI (24 mL, 177 mmol). The reaction mixture was stirred at 60C overnight. After cooling to r.t., the mixture was filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to afford compound 15d (32 g, 58%).[00155] This compound was characterized by proton NMR (1HNMR) and mass spectroscopy (MS) in accordance with the procedures described herein. Proton NMR yielded the following results: 1H NMR (DMSO-d6, 400MHz): delta 8.13(s, 1 H), 7.23(d, J = 8.8 Hz, 2H), 6.90(d, J = 8.8 Hz, 2H), 5.29(s, 2H), 4.24 (q, J = 6.8 Hz, 2H), 3.71 (s, 3H); 1.26(t, J = 6.8 Hz, 3H). Mass spectroscopy indicated MS (ESI): m/z 387 (M+H)+.

The synthetic route of 179692-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ADDEX PHARMA SA; LIVERTON, Nigel, J.; BOLEA, Christelle; CELANIRE, Sylvain; LUO, Yunfu; WO2012/6760; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics