Tag: M.W:200-300

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, Computed Properties of C14H19N3

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

Related Products of 1029413-51-1, The chemical industry reduces the impact on the environment during synthesis 1029413-51-1, name is 4-Amino-1-(1-boc-azetidin-3-yl)-1H-pyrazole, I believe this compound will play a more active role in future production and life.

C) tert-butyl 3-(4-((4-((3S)-3-cyano-3-cyclopropyl-2-oxopyrrolidin-1-yl)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)azetidine-1-carboxylate To a solution of (3S)-1-(2-chloropyrimidin-4-yl)-3-cyclopropyl-2-oxopyrrolidine-3-carbonitrile (300 mg) obtained in Step E of Example 103, tert-butyl 3-(4-amino-1H-pyrazol-1-yl)azetidine-1-carboxylate (300 mg) obtained in Step B of Example 131, cesium carbonate (740 mg) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (110 mg) in tetrahydrofuran (10 mL) was added tris(dibenzylideneacetone)dipalladium(0) (105 mg), and the mixture was stirred at 90C for 10 hr under argon atmosphere. The solvent was evaporated under reduced pressure, and the reaction mixture was poured into water, and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (310 mg). MS(ESI+): [M+H]+ 465.4.

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-Amino-1-(1-boc-azetidin-3-yl)-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; TSUKAMOTO, Tetsuya; OHBA, Yusuke; YUKAWA, Takafumi; NAGAMIYA, Hiroyuki; KAMEI, Taku; TOKUNAGA, Norihito; SAITOH, Morihisa; OKABE, Atsutoshi; EP2832734; (2015); 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)-lH-pyrazole-l -acetic acid (0.8 g, 3.8 mmol) in dichloromethane (10 mL) was added oxalyl chloride (2.4 g, 19.2 mmol) and two drops of iV.TV-dimethylformamide, resulting in slight exothermicity. The reaction mixture was then heated at reflux for 15 minutes. The reaction mixture was concentrated in vacuo, and the residue was suspended in tetrahydrofuran (10 mL) and treated with a solution of 2-(4-piperidinyl)-4-thiazolecarboxaldehyde’ monohydrochloride (i.e. the product of Example 2, Step A) (1.1 g, 5.1 mmol) in tetrahydrofuran (10 mL), followed by dropwise addition of triethylamine (1.2 g, 11.9 mmol). The reaction mixture was stirred overnight at room temperature and then partitioned between 1 N aqueous hydrochloric acid and ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with additional ethyl acetate (2 x 30 mL). The combined organic layers were washed with 1 N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate solution, and brine. The organic layer was dried (MgSC^) and evaporated under reduced pressure to give 0.8 g of the title compound as a yellow oil. IH NMR (CDCl3) delta 1.79-1.90 (m, 2H)5 2.18-2.29 (m, 2H), 2.33 (s, 3H), 2.87-2.94 (m, IH)5 3.28-3.40 (m, 2H), 4.05-4.15 (m, IH), 4.56-4.64 (m, IH), 4.99-5.02 (m, 2H), 6.35 (s, IH), 8.12 (s, IH)5 IO-Ol (s, IH).; To a solution of 5-methyl-3-(trifluoromethyl)-li’-pyrazole-l -acetic acid (0.5 g,2.4 mmol) in dichloromethane (4 mL) was added oxalyl chloride (0.3 mL, 3.6 mmol) and one drop of N,LambdaT-dimethylformamide, resulting in slight exothermicity. The reaction mixture was then heated at reflux for 15 minutes. The reaction mixture was evaporated, and the resulting residue was suspended in dichloromethane (4 mL) and treated with a solution of 4-(4-ethenyl-2-thiazolyl)piperidine (i.e. the product of Example 4, Step B) (302 mg,1.5 mmol) in dichloromethane (2 mL), followed by addition of triethylamine (0.32 mL, 2.3 mmol). The reaction mixture was stirred overnight at room temperature, then concentrated, and purified by column chromatography on silica gel using 30-40 % ethyl acetate in hexanes as eluant to give 414 mg of the title compound as a white solid. IH NMR (CDCl3) 6 1.78 (m, 2H), 2.18 (m, 2H), 2.32 (s, 3H), 2.90 (br t, IH), 3.30 (m, 2H),4.03 (d, IH), 4.55 (d, IH), 5.00 (m, 2H), 5.35 (d, IH), 6.02 (d, IH), 6.33 (s, IH), 6.68 (dd,IH)5 7.01 (s, IH).

According to the analysis of related databases, 345637-71-0, 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; WO2008/13622; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 39806-90-1,Some common heterocyclic compound, 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole, molecular formula is C4H5IN2, 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.

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.

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

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

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

Synthetic Route of 155377-19-8,Some common heterocyclic compound, 155377-19-8, name is Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate, molecular formula is C7H7F3N2O2, 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 solution of ethyl 3- {trifluoromethyl) -lH-pyrazole-4- carboxylate (0.208 g, 1.0 mmol) in DMF were added lH-indol-5- ylboronic acid (0.322 g, 2.00 mmol), Cu(OAc)2 (0.136 g, 0.75 rninol)/ and pyridine (0.162 ml, 2.00 mmol) and the mixture was stirred at room temperature for 3 days . The mixture was diluted with DCM and filtered through a pad of silica gel. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (3:1 hexanes/EtOAc) to give ethyl 1- (lH-indol-5-yl) -3- (trifluoromethyl) -lH-pyrazole-4- carboxylate (0.313 g, 97%) as a solid: 1H NMR (CDCl3) delta 1.39 (t, 3H7 J = 7.0 Hz), 4.37 Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/11131; (2008); 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. Recommanded Product: 51516-70-2

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

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

Reference of 1280210-79-8,Some common heterocyclic compound, 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, molecular formula is C10H15N3O2, 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.

4,6-Dihydro-2H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester (0.50 g, 2.39 mmol) was dissolved in tetrahydrofuran (15 mL).Nitrogen protection,Sodium hydride (0.19 g, 4.77 mmol, 60%) was added at 0 C, and the mixture was slowly warmed to room temperature for 1 hour.Cool down to 0 C,Thiophene-2-sulfonyl chloride (0.65 g, 3.58 mmol) was added and allowed to react at room temperature for 15 hours.The reaction was quenched with water (10 mL) EtOAc.The combined organic phases were washed with a saturated sodium chloride solution (10 mL).Dry over anhydrous sodium sulfate and concentrate by suction filtration.The residue was subjected to silica gel column chromatography[ethyl acetate/petroleum ether (v/v) = 1/4] purified,The title compound was obtained (0.71 g, 84%).It is a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, its application will become more common.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ruyuan Yong Xing Technology Services Co., Ltd.; Li Jianhao; Gu Zheng; Deng Xinshan; Tang Wanjun; Zhang Zongyuan; Kang Panpan; Yuan Weihui; Peng Fei; (49 pag.)CN109942583; (2019); A;,
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. COA of Formula: C5H8BrN3O2S

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