Tag: M.W:100-200

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 3524-32-1, name is 5-Amino-1,3-dimethylpyrazole, A new synthetic method of this compound is introduced below., Formula: C5H9N3

Example 16; Synthesis of (S^-bis-trifluoromethyl-benzy^-t-Ccyclopentylmethyl-ethyl-amino)- ljS-dimethyl-lH-pyrazololS^-ZjJpyridine-S-ylmethyll-carbamic acid methyl ester; Step (i): Synthesis of N-(2,5-dimethyl-2H-pyrazol-3-yl)-acetamide; Pyridine (7,1 mL, 90 mmol) was added to a solution of 2,5-dimethyl-2H-pyrazol- 3-ylamine (10 g, 90 mmol) in acetic anhydride (46 mL) at 0 0C and the resulting mixture was stirred at room temperature for 30 min. The solvent was removed under vacuum to yield the title compound as a brownish liquid (13.7 g), yield: 100%. 1H NuMR (400 MHz, CDC13): delta 7.91 (bs, IH), 5.98 (s, IH), 3.67-3.56 (m, 3H), 2.19-2.11 (m, 6H). ES-MS m/z 154 (M++ 1, 100%).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; REDDY US THERAPEUTICS, INC.; BARUAH, Anima; DE, Dibyendu; KHANNA, Ish Kumar; PILLARISETTI, Sivaram; MAITRA, Santanu; ALEXANDER, Christopher, W.; SREENU, Jennepalli; DAGER, Indu; WO2006/73973; (2006); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 3524-32-1, The chemical industry reduces the impact on the environment during synthesis 3524-32-1, name is 5-Amino-1,3-dimethylpyrazole, I believe this compound will play a more active role in future production and life.

To a solution of 11.1 g (0.1 mol) of 5-amino-1,3-dimethylpyrazole, obtained in the above step, in 125 cm3 of absolute ethanol were added dropwise 1cm3 of 12 N hydrochloric acid and then 13.5 cm3 of isoamyl nitrite, at 0 C. The solution was subsequently warmed to and left at room temperature for 4 hours. The reaction medium was then filtered on a sinter funnel and the precipitate obtained was washed with 100 cm3 of isopropyl ether. After drying under vacuum at room temperature, 7.5 g of 5-amino-1,3-dimethyl-4-nitroso-pyrazole were obtained in the form of an orange-coloured solid, the melting point of which was from 169 to 171 C.

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, 5-Amino-1,3-dimethylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; L’Oreal; US6338741; (2002); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 127107-23-7, 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. 127107-23-7, name is 1-Methyl-1H-pyrazol-4-amine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

A 25 mL round-bottom flask was charged with intermediate 46.3 (462 mg, 1.17 mmol, 1.00 equiv), n-BuOH (5 mL), 1-methyl-1H-pyrazol-4- amine hydrochloride (187 mg, 1.40 mmol, 1.20 equiv) and HC1 in 1,4-dioxane (0.5 ml). The reaction was stirred for 16 hours at 110 C in an oil bath. The resulting mixture was concentrated under vacuum and diluted with 0.5 mL of sodium carbonate (1 mol/L). To this mixture was added 1 mL of methanol, and the resulting solution was extracted with 3 x 20 mL of CHC13/1PA3: 1. The organic layers were combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified using preparative HPLC to furnish 45.7 mg (9%) of compound 1-47 as a white solid. LCMS (ES, m/z): 457 [M+H], ?H NMR (300 MHz ,CD3OD): oe 7.869 (1H, s), 7.564 (1H, s), 4.8684.597 (1H, s), 4.0454.054 (1H, s), 3.888 (3H, s) 3.736 (4H, t), 2.5592.658 (4H, s), 2.2062.423 (3H, s), 2.0412.103 (2H, m), 1.3111.534 (1OH, m).

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-pyrazol-4-amine hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NIMBUS IRIS, INC.; ROMERO, Donna L.; MASSE, Craig E.; ROBINSON, Shaughnessy; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine; WO2015/48281; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 84547-61-5, The chemical industry reduces the impact on the environment during synthesis 84547-61-5, name is (1-Methyl-1H-pyrazol-5-yl)methanol, I believe this compound will play a more active role in future production and life.

Production Example 32 2-[(1-Methyl-1H-pyrazol-5-yl)methoxy]-5-(trifluoromethyl)pyridine Under a nitrogen atmosphere, a mixture of (1-methyl-1H-pyrazol-5-yl)methanol (200 mg), 2-chloro-5-(trifluoromethyl)pyridine (389 mg), palladium(II) acetate (40 mg), cesium carbonate (870 mg), rac-2-(di-t-butylphosphino)-1,1′-binaphthyl (71 mg) and toluene (9.0 mL) was stirred at 100 C. for 2.5 hours. Thereafter, the reaction solution was diluted with diethyl ether, and was then filtrated with Celite. The filtrate was concentrated under a reduced pressure. The residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=85:15 to 50:50), so as to obtain the title compound (310 mg) in the form of a light yellow oily substance. 1H NMR (200 MHz, CHLOROFORM-d) delta ppm 3.95 (s, 3H) 5.44 (s, 2H) 6.36 (d, J=1.76 Hz, 1H) 6.85 (d, J=8.79 Hz, 1H) 7.45 (d, J=2.20 Hz, 1H) 7.80 (dd, J=8.79, 2.64 Hz, 1H) 8.47 (s, 1H); MS (ESI pos.) m/z: 258 [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, (1-Methyl-1H-pyrazol-5-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; Nakamura, Toshio; Sakagami, Kazunari; Konishi, Kazuhide; Yamamoto, Kanako; Masuda, Seiji; Matsuda, Yohei; Okada, Kumiko; Shibata, Tsuyoshi; Ohta, Hiroshi; Yasuhara, Akito; Kawamoto, Hiroshi; US2013/123500; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 27006-76-4, name is 5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxaldehyde, 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 27006-76-4, name: 5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxaldehyde

General procedure: To a solution of substituted phenol (26 mmol) in absolute ethanol (50 mL) was added sodium hydroxide (26 mmol) at room temperature. The mixture was heated to reflux for 3-5 h. After the removal of the solvent, the residue was dissolved in dimethylsulfoxide (50 mL), to the resulting mixture was added 5-chloro-1,3-dimethyl-1H-pyrazole-4-carbaldehyde (5) (20 mmol) in portions. Then the solution was heated to 105 C and maintained at that temperature for 4-15 h and cooled to room temperature. The reaction mixture was poured into water (100 mL) and extracted with ethyl acetate (3 50 mL). The organic layer was washed with water (3 25 mL) and dried over anhydrous Na2SO4, filtered and evaporated to produce the corresponding carbaldehydes 6d-6w, with yields ranging from 60% to 81% [11].

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Dai, Hong; Chen, Jia; Li, Hong; Dai, Baojiang; He, Haibing; Fang, Yuan; Shi, Yujun; Molecules; vol. 21; 3; (2016);,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1190380-49-4, 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. 1190380-49-4, name is 1-(Tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-amine, This compound has unique chemical properties. The synthetic route is as follows.

1-(Oxan-4-yl)-1 H-pyrazol-4-amine (51 mg, 0.303mmol) was added to a solution of A7 (59mg, 0.151 mmol) in dioxane (2mL). The reaction mixture was stirred at 70C for 17h. The mixture was diluted with EtOAc (30ml_) and was washed with sat aq NaHC03 (2 x 10ml_) and brine (2 x 10ml_) before drying over MgS04 and cone, in vacuo. The crude reaction mixture was purified by preparative TLC on silica, eluting with 5% MeOH/10% iPr20/CH2CI2 to give the title compound as a white solid (19mg, 26%). 1H NMR (500MHz, CDCI3 + 1 drop DMSO-d6) 8.52-8.50 (1 H, m), 8.31-8.11 (1 H, m), 7.97-7.92 (1 H, m), 7.62 (1 H, s), 7.27-7.20 (4H, m), 5.83-5.65 (2H, m), 4.40-4-27 (1 H, m), 4.18-4.08 (2H, m), 3.76-3.62 (2H, m), 3.61-3.48 (2H, m), 3.18-3.04 (3H, m), 2.15-2.03 (5H, m). LCMS (Method 1 ) Rt 1 .883min. ESIMS m/z [M+H]+ 475.2.

The chemical industry reduces the impact on the environment during synthesis 1-(Tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BIONOMICS LIMITED; HARVEY, Andrew John; RIPPER, Justin Anthony; HUFF, Belinda Cheryl; PAUL, Dharam; WO2015/123722; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 402-61-9, 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. 402-61-9, name is 5-Methyl-1H-pyrazole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

In similar way, Cu(ClO4)26H2O (2.25mmol, 0.83g) in 20mL dry methanol is mixed with a dry methanolic solution (15mL) of Hmpca (5mmol, 0.63g). The resulting solution is refluxed for 4h; slow evaporation of the solution at room temperature furnished blue crystalline compound which is filtered off, washed with methanol and dried over silica gel. The yield is 0.51g (68%) for [Cu(mpca)2]H2O( 2). Elemental analysis for 2 (when n1) (C10H12CuN4O5): Calculated: C, 36.16; H, 3.61; N, 16.87 and Found: C, 36.29; H, 3.42; N, 16.91. IR assignments (in cm1): m(CN) (1369), m(C-N) (1285), m(N-N) (1034) and m(C-O) (1550).

The chemical industry reduces the impact on the environment during synthesis 5-Methyl-1H-pyrazole-3-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Article; Santra, Ananyakumari; Brandao, Paula; Jana, Harekrishna; Mondal, Gopinath; Bera, Pradip; Jana, Abhimanyu; Bera, Pulakesh; Journal of Coordination Chemistry; vol. 71; 22; (2018); p. 3648 – 3664;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 578008-32-9, A common heterocyclic compound, 578008-32-9, name is tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate, molecular formula is C9H15N3O2, 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.

Example 10; 3-{[4-(Azetidin-l-ylcarbonyl)phenvnoxy}-iV-(5-methyl-lH-pyrazol-3-yl)- 5- [(3S)-tetr ahydrofur an-3-yloxyl benzamide; l-Chloro-N,N,2-trimethyl-l-propenylamine (0.145 mL, 1.10 mmol) was added to a solution of 3-{ [4-(azetidin- 1 -ylcarbonyl)phenyl]oxy } -5-[(3S)-tetrahydrofuran-3- yloxy]benzoic acid (350 mg, 0.92 mmol) in DCM (6 mL) and stirred at RT for 30 – 40min. 1,1-Dimethylethyl 3-amino-5-methyl-lH-pyrazole-l-carboxylate (361 mg, 1.83 mmol) and pyridine (0.148 mL, 1.83 mmol) were added and the reaction stirred at RT for 2 hours. The solvent was removed in vacuo, water (20 mL) added and the mixture extracted with ethyl acetate (3 x 20 mL). The extracts were combined and washed with 2Nu hydrochloric acid (20 mL), a saturated solution of sodium bicarbonate (20 mL), water (20 mL), brine (20 mL), dried (MgSO4) and evaporated in vacuo. The crude product was chromatographed on silica, eluting with a gradient of 0- 10% methanol in DCM, to give a white solid which was taken up in acetonitrile (2 mL) and heated in a microwave reactor at 160C for 10 minutes. EPO The reaction mixture was evaporated and the residue chromatographed on silica, eluting with 0-5% methanol in DCM, to give the desired compound as a white foam (50 mg). 1H NMR delta (CDCl3): 2.11 – 2.29 (m, 2H), 2.32 (s, 3H), 2.32 – 2.40 (m, 2H), 3.88 – 4.02 (m, 4H), 4.23 (t, 2H), 4.35 (t, 2H), 4.95 – 4.99 (m, IH), 6.56 (s, IH), 6.71 (t, IH), 7.02 (d, 2H), 7.13 (s, IH), 7.21 (s, IH), 7.64 (d, 2H), 9.06 (s, IH); m/z 463 (M+H)+, 461 (M-H)’

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/17649; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 25016-12-0,Some common heterocyclic compound, 25016-12-0, name is 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde, molecular formula is C6H8N2O, 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: To a solution of Example 13 (53 mg, 0.17 mmol, 1.0 eq) and 1-methyl-1H-imidazole-2-carbaldehyde (28 mg, 0.25 mmol, 1.5 eq) in THF (2 mL) under a N2 atmosphere was added NaBH(OAc)3 (72 mg, 0.34 mmol, 2.0 eq) and the mixture was stirred at RT overnight. The mixture was purified by C18 reverse phase column (Biotage, 30% to 70% ACN in water, 0.1% TFA) to afford the title compound (22 mg, 34%) as a white solid. LCMS: [M+H]+ 384.2. 1H NMR (400 MHz, CDCl3) delta 8.10 (d, J=8.4 Hz, 1H), 7.65 (d, J=7.2 Hz, 1H), 7.41 (s, 2H), 7.20 (s, 1H), 4.78 (s, 2H), 3.98 (s, 3H), 3.80 (s, 2H), 3.40 (m, 2H), 3.17-3.00 (m, 3H), 2.59 (s, 3H), 2.24 (m, 2H), 1.95 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde, its application will become more common.

Reference:
Patent; Ribon Therapeutics Inc.; Schenkel, Laurie B.; Vasbinder, Melissa Marie; Kuntz, Kevin Wayne; Swinger, Kerren Kalai; (179 pag.)US2019/194174; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 127107-23-7, name is 1-Methyl-1H-pyrazol-4-amine hydrochloride, A new synthetic method of this compound is introduced below., name: 1-Methyl-1H-pyrazol-4-amine hydrochloride

The 2,5-dichloro-N-(6-methoxyhexahydrofuro[3,2-b]furan-3-yl)pyrimidin-4-amine (430mg, 1.4046 mmol), diisopropylethylamine (546.7 mg, 4.23 mmol) and 1-methylpyrazol-4-amine hydrochloride (283.3 mg,2.12 mmol) was dissolved in n-BuOH (10 mL), the temperature of the reaction solution was raised to 150 C, sealed tube reaction for 23 hours, and then concentrated under reduced pressure.The residue was purified by silica gel column chromatography (DCM / MeOH (v / v) = 50/1) to afford the title compound as a white solid which was recrystallized from acetone to give the title compound as a white solid (220 mg, 42.6% ).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Li Minxiong; Li Xiaobo; Dai Weilong; Wang Tingjin; (74 pag.)CN104926824; (2017); B;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics