pyrazoles-derivatives

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. 821767-61-7, name is tert-Butyl 4-formyl-1H-pyrazole-1-carboxylate, A new synthetic method of this compound is introduced below., Safety of tert-Butyl 4-formyl-1H-pyrazole-1-carboxylate

Tert-Butyl 4-formyl-1H-pyrazole-1-carboxylate (CAS [821767-61-7]), (122 mg, 0.62 mmol) was added at 10 C, under N2 to a solution of intermediate 15 (183 mg, 0.55 mmol) in MeOH (7 mL). The mixture was stirred at rt for 5 h. Then NaBH4 (31 mg, 0.83 mmol) was added portionwise and the mixture was stirred at rt for 15 h. The mixture was poured into ice water, extracted with DCM. The organic layer was dried over MgSO4, filtered and evaporated to dryness giving 0.35g of crude compound. The residue was purified by chromatography over silica gel (Stationary phase: irregular SiOH 15-40mum 40g, Mobile phase: Gradient from 0.1% NH4OH, 97% DCM, 3% MeOH to 0.1% NH4OH, 95% DCM, 5% MeOH). The fractions containing product were collected and evaporated to dryness yielding 150 mg (yield 39%) of intermediate 17.

The synthetic route of 821767-61-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; PANDE, Vineet; HERKERT, Barbara; KROSKY, Daniel, Jason; QUEROLLE, Olivier, Alexis, Georges; PATRICK, Aaron, Nathaniel; PILATTE, Isabelle, Noelle, Constance; (157 pag.)WO2018/109088; (2018); A1;,
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Synthetic Route of 920006-32-2,Some common heterocyclic compound, 920006-32-2, name is 1-Isopropylpyrazole-5-carboxylic Acid, molecular formula is C7H10N2O2, 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.

1-(propan-2-yl)-1H-pyrazole-5-carboxylic acid (37.8 mg, 245 pmol), HATU (108 mg, 283 pmol), and N,N-diisopropylethylamine (99 mI, 570 mihoI), were dissolved in 3 mL of the N,N-dimethylformamide and the resulting mixture was stirred at room temperature for 15 min, then tert-butyl 3-amino-5-(3,5-dicyano-1,2,6-trimethyl-1,4-dihydropyridin-4-yl)-7-ethyl-6-fluoro-1H-indazole-1-carboxylate (100 mg, 85 % purity, 189 pmol) was added and the resulting mixture was stirred at 90 C for 16 h. The resulting mixtur e was diluted by addition of water and extracted with ethyl acetate, the combined organic phases was washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by prep-HPLC (Column: XBridge Prep C18 OBD Column 19x150mm, 5 pm; Mobile Phase A: Water (10 mmol/L NH4HC03), Mobile Phase B: ACN; Flow rate: 20 mUmin; Gradient: 25% B to 65% B in 7 min; Detector: 254 nm, 220 nm) to give 39.9 mg (43% yield) of the product as a light yellow solid. LC-MS [Water(0.05%TFA)-Acetonitrile, 5%B]: Rt = 1 .38 min. MS (ESIpos): m/z = 487 (M+H)+. 1H-NMR (400 MHz, DMSO-d6) d [ppm]: 1 .24 (t, 3H), 1 .44 (d, 6H), 2.23 (s, 6H), 2.90 (q, 2H), 3.20 (s, 3H), 4.66 (s, 1H), 5.50-5.56 (m, 1H), 7.16 (s, 1H), 7.53-7.55 (m, 1H), 7.59 (s, 1H), 10.85 (s, 1H), 13.12 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Isopropylpyrazole-5-carboxylic Acid, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; HEINRICH, Tobias; CHRIST, Clara; BRIEM, Hans; FARIA ALVARES DE LEMOS, Adelaide, Clara; BADER, Benjamin; HOLTON, Simon; BOeMER, Ulf; LIENAU, Philip; KUHNKE, Lara, Patricia; (122 pag.)WO2019/185525; (2019); A1;,
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These common heterocyclic compound, 54384-74-6, name is 1,5-Dimethylpyrazole-3-carboxamide, 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. Application In Synthesis of 1,5-Dimethylpyrazole-3-carboxamide

To the above product (5 g, 35.97 mmol) in THF (70 mL) was added LiAlH4 (4.1 g, 107.89 mmol) in several batches at 00C. The resulting solution was refluxed for 1 hr. The solids were filtered out and the filtrate was concentrated, resulted in 3 g (67%) of 1,5- dimethyl-lH-pyrazol-3-yl)methanamine as yellow oil.

The synthetic route of 1,5-Dimethylpyrazole-3-carboxamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PONIARD PHARMACEUTICALS, INC.; WO2009/139834; (2009); 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. 143426-49-7, name is (4-Pyrazol-1-yl-phenyl)methanol belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C10H10N2O

H) 1- [4- (chloromethyl) phenyl] -lH-pyrazole To a solution of [ 4- ( lH-pyrazol-l-yl ) phenyl] methanol (24.0 g) in 1 , 2-dichloroethane (200 mL) was added dropwise thionyl chloride (26.3 g) under ice-cooling, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was concentrated under reduced pressure, and the residue was washed with tert-butyl methyl ether to give the title compound (23.5 g) . 1HNMR (400 MHz, CDC13) delta 4.62 (2H, s) , 6.48 (1H, t, J = 2.0 Hz), 7.47 (2H, d, J = 8.8 Hz), 7.69 (2H, d, J = 8.8 Hz), 7.73 (1H, d, J = 2.0 Hz), 7.93 (1H, d, J = 2.4 Hz).

The synthetic route of 143426-49-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; YAMADA, Masami; SUZUKI, Shinkichi; SUGIMOTO, Takahiro; NAKAMURA, Minoru; SAKAMOTO, Hiroki; KAMATA, Makoto; WO2015/163485; (2015); A1;,
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Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 920006-32-2, These common heterocyclic compound, 920006-32-2, name is 1-Isopropylpyrazole-5-carboxylic Acid, 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.

Intermediate 941 -(1 -Methylethyl)-1 H-pyrazole-5-carbonyl chloride Thionyl chloride (5 ml) was added to 1-(1-methylethyl)-1 H-pyrazole-5-carboxylic acid (1g) and the reaction was heated at 800C for 5h. The reaction was evaporated, then azeotroped with toluene to give title compound, 856mg. 1H NMR (CDCI3) delta 7.6 (d, 1 H), delta 7.1 (d, 1 H), delta 5.2 (m, 1 H), delta 1.5 (d, 6H).

Statistics shows that 1-Isopropylpyrazole-5-carboxylic Acid is playing an increasingly important role. we look forward to future research findings about 920006-32-2.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/147188; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 199678-06-3,Some common heterocyclic compound, 199678-06-3, name is 4-(1-Methyl-1H-pyrazol-4-yl)benzoic acid, molecular formula is C11H10N2O2, 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 4-(1-methyl-1H-pyrazol-4-yl)benzoic acid (3.5 g, 17.3 mmol) in DCM (100 mL) was added N,O-dimethylhydroxylamine hydrochloride (2.0 g, 20.8 mmol),(dimethylamino)-N,N-dimethyl(3H- [1,2,3 ]triazolo[4, 5 -b]pyridin-3 -yloxy)-methaniminium hexafluorophosphate (7.9 g, 20.8 mmol) and N,N-diisopropylethylamine (8.58 mL, 51.9 mmol). The mixture was stirred at room temperature for 8 h. The reaction mixture was washed with 1 N HC1 (100 mL x 2), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography (petroleum ether / EtOAc = 3 : 1) to give thetitle compound (3.2 g, 75%) as a yellow solid.

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

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy M.; WAI, John; LAI, Kwong Wah; WANG, Fei; CHEN, Kevin X.; (351 pag.)WO2017/205538; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 35852-81-4, 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. 35852-81-4, name is 4-Chloro-1-methyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Azole (1.0 mmol, 1.0 eq.) (if solid), aryl bromide (1.05 mmol, 1.05 eq.) (if solid), (palladium(II) acetate (11 mg, 0.05 mmol, 0.05 eq.), QPhos (53 mg, 0.075 mmol, 0.075 eq.) and tetrabutylammonium acetate (904 mg, 3.0 mmol, 3.0 eq.) were added to a reaction vial (ambient atmosphere). The vial was equipped with a stirring bar and placed under a nitrogen atmosphere. Dioxane (2.50 ml, 0.4M) was added or if liquid, azole/aryl bromide was added as a solution in dioxane (2.50 ml, 0.4M). The mixture was stirred at 80-105 C under nitrogen or microwaved at 120 C for 16-72 h (complete consumption of one of the starting materials or no further progress as monitored by UPLC/MS). The crude reaction mixture was purified by column chromatography. The 1H NMR spectra of the obtained products matched the data reported in the literature.

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

Reference:
Article; Vernier, William F.; Gomez, Laurent; Tetrahedron Letters; vol. 58; 49; (2017); p. 4587 – 4590;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 595610-50-7, 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. 595610-50-7, name is 5-(3-Chlorophenyl)-1H-pyrazole-3-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To amixture of 3-(3-chlorophenyl)-1H-pyrazole-5-carboxylic acid (14a, 133 mg, 0.60 mmol) inDMF(4 mL)was added (S)-methyl-4-(2-amino-3-phenylpropanamido)benzoate hydrochloride (12, 200 mg,0.60 mmol), N,N-diisopropyl-ethylamine (232 mg, 1.80 mmol), 1-hydroxybenzotriazole(161 mg,1.20 mmol) and N-(3-dimethylaminopropyl)-N0-ethylcarbodiimide hydrochloride (229 mg, 1.20 mmol)and the reaction mixture was stirred at room temperature overnight.Then TLC analysis indicatedreaction was complete, and H2O (40 mL) was added.The mixture was stirred for 10 min and filtered toget crude product 13a as a yellow solid, which was used for next step without further purification.

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

Reference:
Article; Wei, Qunchao; Zheng, Zhichao; Zhang, Shijun; Zheng, Xuemin; Meng, Fancui; Yuan, Jing; Xu, Yongnan; Huang, Changjiang; Molecules; vol. 23; 8; (2018);,
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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. 1904-24-1, name is 3-Amino-5-ethylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C5H9N3

Method 65; 4- (5-Ethvl-lH-pyrazol-3-vlamino)-2-chloropyrimidine A mixture of 2, 4-dichloropyrimidine (2.97g, 20mmol), 5-amino-3-ethyl-1H-pyrazole (2.44g, 22mmol) and N, N-diisopropylethylamine (3. 8ml, 22mmol) in dry THF (75ml) was heated at 60C for 18 hours. The volatiles were removed by evaporation, and the residue was triturated with a mixture of DCM and water. The solid product was collected by filtration, washed with water and ether, and dried to give the title compound (1.55g, 35%) as a colourless crystalline solid. NMR (DMSO): 1.20 (t, 3H), 2.60 (q, 2H), 6.06 (s, 1H), 7.15 (s, 1H), 8.10 (d, 1H), 9.80 (s, 1H), 11.83 (br s, 1H); m/z 224 [MH] +.

The synthetic route of 1904-24-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/40159; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 84547-87-5, 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. 84547-87-5, name is 4-Chloro-1H-pyrazole-5-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: [00223] A flask was charged with lH-pyrazole-3-carboxylic acid (5.00 g, 44.6 mmol, 1.00 equiv), t-butanol (50 mL), di-t-butyl dicarbonate (39.0 g, 179 mmol, 4.01 equiv), triethylamine (27.0 g, 268 mmol, 6.00 equiv) and DMAP (1.10 g, 9.00 mmol, 0.20 equiv). The resulting solution was stirred overnight at 65 C and quenched with water (20 mL). The mixture was extracted with EtOAc (3 x 50 mL) and the organic layers were combined, washed with water (3 x 20 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to provide 11.2 g (crude) of di-t-butyl lH-pyrazole-l,3-dicarboxylate as a yellow oil. LCMS (ESI, m/z): 169 [M+H- Boc]+

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-Chloro-1H-pyrazole-5-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; WIENER, John J. M.; WEBER, Olivia D.; DUNCAN, Katharine K.; (364 pag.)WO2018/217805; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics