Day: May 19, 2021

Reference of 436096-96-7, 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 436096-96-7 as follows.

Preparation 68: [3′-(4-Fluorophenyl)-2,3,5,6-tetrahydro-[l,2′]bipyrazinyl-4-yl]-(l- isopropyl-lH-pyrazol-4-yl)-methanone Dissolve l-isopropyl-lH-pyrazole-4-carboxylic acid (0.120 g, 0.780 mmol) inDCM (5 mL). Add etaOBt (0.088 g, 0.650 mmol) followed by l-(3-dimethyl- aminopropyl)-3-ethylcarbodiimide hydrochloride (0.125 g, 0.650 mmol). Add 3′-(4- fluorophenyl)-3,4,5,6-tetrahydro-2eta-[l,2′]bipyrazinyl (0.168 g, 0.650 mmol) and stir at room temperature for 18 hr. Add DCM and water and separate layers. Extract aqueous layer 3 times with DCM, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 25:75 to 100:0 ethylacetate/hexanes), to give the title preparation (211 mg, 82%). MS (ES): m/z = 395 [M+H]+.

According to the analysis of related databases, 436096-96-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2008/141020; (2008); 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. 139756-04-0, name is 1-Methyl-4-(2-propoxybenzamido)-3-propyl-1H-pyrazole-5-carboxamide, A new synthetic method of this compound is introduced below., Product Details of 139756-04-0

EXAMPLE 113 1-Methyl-5-(2-n-propoxyphenyl)-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one 1-Methyl-4-(2-n-propoxybenzamido)-3-n-propylpyrazole-5-carboxamide (0.34 g, 0.99 mmol) was added to a stirred mixture of 30% hydrogen peroxide solution (1.0 ml), potassium carbonate (0.54 g, 3.92 mmol), water (10 ml) and ethanol (5 ml). The mixture was heated under reflux for 38 hours and then evaporated under vacuum. The residue was suspended in water (20 ml), then the mixture acidified with 2N hydrochloric acid and extracted with dichloromethane (3*20 ml). The extracts are combined, dried (Na2SO4) and evaporated under vacuum. The resulting residue was chromatographed on silica gel (6 g), using a methanol in dichloromethane elution gradient (0.0-1.0%), to give an oil, successive trituration of which with ether gave the required product as a white solid (0.19 g, 59%), m.p. 111-114 C. Found: C, 66.26; H, 6.92; N, 17.15. C18H22N4O2 requires C, 66.23; H, 6.80; N, 17.17%.

The synthetic route of 139756-04-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cell Pathways, Inc.; US6200980; (2001); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 90253-21-7, name is 4-Cyclopropyl-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 90253-21-7, HPLC of Formula: C6H8N2

To a 20 ml vial, compound 211 I-135 (25.0 mg, 0.084 mmol) and 195 copper iodide (1.607 mg, 8.44 mumol) were added followed by 213 4-cyclopropyl-1H-pyrazole (9.13 mg, 0.084 mmol) and 196 trans-N,N?-dimethylcyclohexane-1,2-diamine (2.401 mg, 0.017 mmol). This mixture was then evacuated and backfilled with nitrogen (3 times). Then dry, degassed 214 1,2-dioxane (338 mul) was added. The mixture was heated at 110 C. for 24 h and cooled to RT. The crude material was purified by mass-directed reversed phase chromatography (ACN/water gradient with 0.1% 19 TFA modifier) to afford the 215 title compound. MS (ESI) [M+H]+: m/z 324. 1H NMR (600 MHz, DMSO-d6) delta 8.22 (s, 1H), 7.70 (d, J=8.4 Hz, 2H), 7.59 (q, J=6.1, 5.5 Hz, 1H), 7.51 (d, J=18.9 Hz, 1H), 7.39 (d, J=8.4 Hz, 2H), 2.96 (p, J=7.0 Hz, 2H), 2.77-2.62 (m, 2H), 2.33 (dq, J=19.2, 10.1, 9.3 Hz, 2H), 1.86-1.68 (m, 3H), 1.32 (p, J=7.1 Hz, 2H), 0.86 (t, J=6.2 Hz, 2H), 0.70 (t, J=7.3 Hz, 3H), 0.58 (d, J=4.0 Hz, 2H).

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

Reference:
Patent; Merck Sharp & Dohme Corp.; Han, Yongxin; Achab, Abdelghani; Deng, Yongqi; Fradera, Xavier; Gibeau, Craig; Hopkins, Brett A.; Li, Derun; Liu, Kun; McGowan, Meredeth A.; Sciammetta, Nunzio; Sloman, David; White, Catherine; Zhang, Hongjun; Zhou, Hua; US2019/144433; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 1001020-13-8,Some common heterocyclic compound, 1001020-13-8, name is (3-Trifluoromethyl-1H-pyrazol-4-yl)methanol, molecular formula is C5H5F3N2O, 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.

(S)-benzyl-5-(hydiOxymethyl)-2,3-dihydro-7 /-/-inden-2-ylcarbamate (7.13 mmol, 2.12g) was dissolved in DCM (20 ml_), thionyl chloride (14.26 mmol, 1.040 ml_, 1.696 g) added and the resultant solution stirred at room temperature for 45 min. The sample was concentrated and azeotroped with dichloromethane (x 4). Potassium carbonate (21.39 mmol, 2.96 g) was added followed by DMF (20 ml.) and (3-(trifluoromethyl)-1 H-pyrazol-4- yl)methanol (7.13 mmol, 1.184 g) and the mixture heated to 60 0C for 1 h. The mixture was concentrated and partitioned between ethylacetate/water. The aqueous layer was twice extracted with ethylacetate and combined organics dried, filtered and concentrated to give a yellow oil which was purified on silica eluting with 0 – 1 % MeOH/DCM to give (S)-benzyl-5-((4-(hydroxymethyl)-3-(trifluoromethyl)-7/-/-pyrazol-1-yl)methyl)-2,3-dihydro- 7H-inden-2-ylcarbamate as a light coloured oil (2.67 g, 84 %). 1H NMR (400 MHz, CDCI3) delta 1.83 (t, 1 H) 2.79 (m, 2H) 3.27 (m, 2H) 4.51 (bs, 1 H) 4.63 (d, 2H) 4.98 (bs, 1 H) 5.08 (bs, 2h) 5.24 (s, 2H) 7.05-7.1 1 (m, 2H) 7.18 (m, 1 H) 7.26-7.39 (m, 6H).

The synthetic route of 1001020-13-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; N.V. ORGANON; WO2009/147167; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 2654-57-1, These common heterocyclic compound, 2654-57-1, name is 4-Methyl-1-phenylpyrazolidin-3-one, 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.

4-Methyl-1-phenyl-1,2-dihydro-3H-pyrazol-3-one (5) was synthesized in a similar way from 0.17 g (1 mmol) of 4-methyl-1-phenylpyrazolidin-3-one (3) in 1 mL of methylene chloride and 0.19 g (1.01 mmol) of 1 in 1 mL of methylene chloride at room temperature. Yield 0.15 g (88%), yellow powder, mp 209 C [5, 6]. 1H NMR spectrum, delta, ppm: 1.90 s (3H, CH3), 7.12 t (1H, p-H, J = 7.3 Hz), 7.38 t (2H, m-H, J =8.1 Hz), 7.60 d (2H, o-H, J = 7.8 Hz), 8.01 s (1H,=CH), 10.14 (1H, NH). 13C NMR spectrum, deltaC, ppm:7.0, 103.3, 116.2, 123.9, 126.5, 129.3, 139.9, 161.4. The spectral parameters of 5 coincided with those given in [5, 6].

The synthetic route of 2654-57-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shainyan; Tolstikova; Russian Journal of Organic Chemistry; vol. 53; 4; (2017); p. 632 – 633; Zh. Org. Khim.; vol. 53; 4; (2017); p. 624 – 625,2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 137890-05-2, name is 1-(1-Methyl-1H-pyrazol-5-yl)ethanone, 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 137890-05-2, COA of Formula: C6H8N2O

Under N2, a mixture of intermediate 1 lb (1 g) and 5-acetyl-l-methylpyrazole (168mgl.35 mmol) in THF (15 mL) was stirred at rt overnight. Then, NaBH(OAc)3 (718 mg;3.4 mmol) was added portion wise. The reaction mixture was stirred at room temperature for 72h, poured into cold water, basified with K2C03 powder and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and evaporated to dryness. The residue was purified by chromatography over silica gel (irregular SiOH, 12g; mobile phase:gradient from 100% DCM, 0% MeOH to 95% DCM, 5% MeOH, 0.3% NH4OH). The fractions were collected and evaporated to dryness. The residue (300 mg) was purified asecond time by reverse phase chromatography (YMC-actus Triart Cl 8 1 Ojim30*150mm; mobile phase: gradient from 65% NH4HCO3 0.2% aq, 35% ACN to 25%NH4HCO3 0.2% aq, 75% ACN). The pure fractions were collected, evaporated to drynessyielding 104 mg of compound 224.

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:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; PANDE, Vineet; HERKERT, Barbara; KROSKY, Daniel, Jason; QUEROLLE, Olivier, Alexis, Georges; PILATTE, Isabelle, Noelle, Constance; PATRICK, Aaron, Nathaniel; (250 pag.)WO2018/50686; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 916766-83-1, A common heterocyclic compound, 916766-83-1, name is 3-(4-(Chloromethyl)phenyl)-1-methyl-1H-pyrazole, molecular formula is C11H11ClN2, 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.

To a mixture of 3- ( (3S, 4S) -4-hydroxytetrahydro-2H-pyran-3-yl) -7, 8-dimethyl-6- (4,4,5, 5-tetramethyl-l, 3, 2-dioxaborolan-2- yl) -2H-benzo [e] [1, 3] oxazin-4 (3H) -one (0.06 g), 3-(4- (chloromethyl) phenyl) -1-methyl-lH-pyrazole (0.03 g) and 2 M aqueous sodium carbonate solution (0.16 mL) in DME (3 mL) -water (0.3 mL) was added 1, 1′ -bis (diphenylphosphino) ferrocenepalladium (II) chloride (0.01 g) , and the mixture was subjected to microwave irradiation at 110C for 50 min. The. reaction mixture was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue waspurified by NH silica gel column chromatography (ethylacetate/hexane) and solidified with ethanol to give the title compound (0.02 g) .XH NMR (300 MHz, DMSO-d6) delta 1.39-1.60 (1H, m) , 1.83-1.97 (1H, m) , 2.11 (3H, s), 2.16 (3H, s) , 3.33-3.54 (2H, m) , 3.64-3.74 (1H, m) , 3.86 (6H, s) , 4.00 (2H, s) , 5.06 (1H, d, J = 5.3 Hz) , 5.20-5.40 (2H, m) , 6.61 (1H, d, J = 2.1 Hz), 7.12 (2H, d, J = 8.3 Hz), 7.46 (1H, s) , 7.63-7.73 (3H, m) .

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; SUGIMOTO, Takahiro; SUZUKI, Shinkichi; SAKAMOTO, Hiroki; YAMADA, Masami; NAKAMURA, Minoru; KAMATA, Makoto; SHIMOKAWA, Kenichiro; OGINO, Masaki; KIMURA, Eiji; MURAKAMI, Masataka; YONEMORI, Jinichi; KOJIMA, Takuto; (281 pag.)WO2016/208775; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 38858-90-1, The chemical industry reduces the impact on the environment during synthesis 38858-90-1, name is 4-Methyl-3-nitro-1H-pyrazole, I believe this compound will play a more active role in future production and life.

A solution of 4-methyl-3-nitro-1H-pyrazole (500 mg, 3.93 mmol), iodomethane (837.9 mg, 5.9 mmol) and potassium tert-butoxide (484.6 mg, 4.33 mmol) in tetrahydrofuran (20 mL) was stirred at 25 C. for 1 hour. The solvent was concentrated under vacuum. The residue was purified by flash chromatography on silica gel eluting with dichloromethane/methanol (10/1) to afford 1,4-dimethyl-3-nitro-pyrazole (450 mg, 3.18 mmol) as a white solid. LCMS (ESI) [M+H]+=142

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-Methyl-3-nitro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Lainchbury, Michael; Gancia, Emanuela; Seward, Eileen; Madin, Andrew; Favor, David; Fong, Kin Chiu; Hu, Yonghan; Good, Andrew; US2018/282282; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 27412-71-1, name is 5-Phenyl-1H-pyrazol-3(2H)-one belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 27412-71-1

Synthesis of 5-Phenyl-1H-pyrazol-3-yl 1-(2,2,2-trifluoroacetyl)indoline-5-sulfonate (8) and 5-phenyl-1H-pyrazol-3-yl indoline-5-sulfonate (9). Added anhydrous potassium carbonate (1.6 g, 12.5 mM) to a cold solution of 5-phenyl-1H-pyrazol-3(2H)-one (7,1 g, 6.25 mM) and (1-(2,2,2-trifluoroacetyl)indolin-5-ylsulfonyl chloride (2.0 g, 6.39 mM) in DMF and stirred the reaction mixture for 2 h at room temperature. After completion of the reaction was confirmed by TLC, the reaction mixture was mixed with ice cold water and extracted with ethyl acetate. Organic layer was dehydrated with anhydrous sodium sulfate and evaporated under reduced pressure. The crude solid was subjected to column chromatography to separate 8 and 9.

The synthetic route of 27412-71-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Subramanian, Santhosh; Sharma, Vinay K.; Yun, Jieun; Jung, Sang-Hun; Bulletin of the Korean Chemical Society; vol. 35; 10; (2014); p. 2922 – 2928;,
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 19959-77-4 as follows. Computed Properties of C9H9N3

A 5mL ethanol solution of L (0.1mmol, 15.9mg), hydrazine hydrate (0.1mmol, 5mg) and Et3N (0.1mmol, 14mul) was mixed with a 5mL ethanol solution of NiCl2·6H2O (0.05mmol, 11.9mg), and the resulting mixture was then stirred for 15min to obtain a light-green solution. This resulting solution was filtered and left to evaporate for three days, giving rise to light-blue block crystals of 2. The resulting crystals were washed with n-hexane 2?3 times, then dried in vacuum. Yield: 26.4mg (53%), M. p. >300C. Anal. Calc. for C18H24Cl2N7NiO2 (FW, 500.05): C, 43.37; H, 4.86; N, 19.68. Found: C, 43.54; H, 4.96; N, 19.18%. Selected IR data (cm-1, KBr): 3350 (b, m), 3250 (b, s), 3130 (s), 3066 (s), 2969 (s), 2863 (s), 1610 (m) (nu(C=N)), 1573 (m) (nu(C=C)), 1443 (s) (delta(CH3)), 1304 (m) (nu(C-N)), 1256 (w), 1116 (w), 1054 (w), 1021(w), 985 (m), 789 (s).

According to the analysis of related databases, 19959-77-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhu, Guang-Zhou; Xing, Bei-Bei; Yang, Feng-Lei; Li, Xiu-Ling; Polyhedron; vol. 81; (2014); p. 705 – 714;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics