Category: 25016-20-0

Adding a certain compound to certain chemical reactions, such as: 25016-20-0, name is 1-Methyl-1H-pyrazole-3-carboxylic acid, 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 25016-20-0, Product Details of 25016-20-0

1-methyl-1H-pyrazole-5-carboxylic acid (35 mg, 0.28 mmol, 1.1 equiv.), HATU (109 mg, 0.29 mmol,1.15equiv.), DIPEA (37mg, 0.29mmol, 1.15equiv.) is dissolved in an appropriate amount of DMF, stirred for 10 minutes and then added (4-fluoro-2-(Trifluoromethyl)phenyl)(5-aminoindolin-1-yl)methanone (81 mg, 0.25 mmol, 1.0 equiv.), stirring at room temperature for 8 hoursTime. The TLC monitors the reaction in real time. After the reaction, dilute with water, extract the appropriate amount of ethyl acetate three times, combine the organic phase, and then use water,The mixture was washed with saturated NaHCO3 solution and saturated NaCl solution, and the organic layer was dried over anhydrous NaSO?Purification afforded N-(1-(4-fluoro-2-(trifluoromethyl)benzoyl)indolin-5-yl)-1-methyl-1H-pyrazole-3-carboxamide(80 mg, yield: 74%).

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

Reference:
Patent; Fudan University; Wang Yonghui; Yu Fazhi; Li Wei; (38 pag.)CN109232358; (2019); A;,
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. 25016-20-0, name is 1-Methyl-1H-pyrazole-3-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C5H6N2O2

Compound 1025; (2R.6S, 12Z, 13aS, 14aR, 16aS)-2-{[7,8-dichloro-2-(propan-2-yloxy)quinolin-4-yl]oxy}- N-[(1-methylcyclopropyl)sulfonyl]-6-{[(1-methyl-1H-pyrazol-3-yl)carbonyl]amino}- 5,16-dioxo-1, 2,3,6,7,8,9,10,11, 13a,14,15,16,16a- tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-; Step V. Coupling with R2a; Macrocydic Brosylate E (1.01 g, 1.26 mmol) is dissolved in 4 N HCI/dioxanes (5 mL) then stirred for 45 mins and concentrated in vacuo. The residue is redissolved in DCM (10 mL), TEA (0.90 mL, 6.5 mmol), TBTU (485 mg, 1.51 mmol) and 1-methyl- 1H-pyrazole-3-carboxylic acid (R2a, 206 mg, 1.64 mmol) are added. The reaction mixture is stirred for 4 h at RT. The reaction mixture is concentrated in vacuo and the resulting material purified by flash chromatography using DCM/MeOH (0 – 10%). The pure fractions are combined and concentrated in vacuo to give intermediate Ga.

The synthetic route of 25016-20-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LLINAS-BRUNET, Montse; BORDELEAU , Josee; GODBOUT, Cedrickx; LEBLANC, Melissa; MOREAU, Benoit; O’MEARA, Jeffrey; WO2011/63501; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 25016-20-0, A common heterocyclic compound, 25016-20-0, name is 1-Methyl-1H-pyrazole-3-carboxylic acid, molecular formula is C5H6N2O2, 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.

i-Methyl-I H-pyrazole-3-carboxylic acid (48.8 mg) was dissolved in a solution of DMF (3 ml_), DIPEA (182 mul_) and HATU (201 mg), the reaction was stirred at room temperature for 15 mins. Intermediate 64 (150 mg) in DMF (1 ml.) was added and the reactions were stirred at 5O0C under nitrogen for 22 h. The reaction mixture was evaporated in vacuo and was partitioned between DCM and saturated sodium bicarbonate solution. The organic phase was collected and dried by passing through a hydrophobic frit and evaporated in vacuo. The crude material was purified using a 12 g silica ISCO cartridge eluting with a gradient of 5 – 100% EtOAc in cyclohexane to give the title compound. MS calcd for (C29H34N4O4S + H)+ : 535 MS found (electrospray) : (M+H)+ = 535

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; SMITHKLINE BEECHAM CORPORATION; WO2008/59042; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 25016-20-0, The chemical industry reduces the impact on the environment during synthesis 25016-20-0, name is 1-Methyl-1H-pyrazole-3-carboxylic acid, I believe this compound will play a more active role in future production and life.

Acid R2a (9.3 mg, 0.074 mmol) is dissolved in DCM (2 mL), then TEA (41 mu, 0.295 mmol) is added followed by TBTU (21.7 mg, 0.068 mmol). This solution is stirred for 15 mins, after which the amine hydrochloride Ce (50 mg, 0.059 mmol) is added. The resulting solution is stirred at RT for 16 h and then concentrated. The residual is dissolved in DMSO. The resulting solution is filtered through a Millex filter and purified by prep HPLC (Ammonium formate/MeOH). The pure fractions are combined, concentrated redissolved in MeCN and water, frozen and lyophilized to provide compound 1015.FIA M.S.(electrospray) : 804.5 (M-H)” Retention time (min): 5.2 min1H NMR (400 MHz,DMSO-d6): delta 9.57 (s, 1 H) , 7.76 (d, 1 H, J = 2.4 Hz), 7.67 (bs, 1 H). 7.64 (d, 1 H, J = 9 Hz), 6.88 (d, 1 H, J = 9 Hz), 6.59 (d, 1 H, J = 2.1 Hz), 6.24 (s, 1 H), 5.47 (S, 1 H, J = 6.1 Hz), 5.41-5.31 (m, 3H) 4.81-4.73 (m, 1 H), 4.46 (dd, 1 H, J = 7.8, 7.6 Hz), 4.30-4.13 (m, 2H) 3.90 (s, 3H), 2.46-2.41 (m, 2H), 2.38 (s, 3H), 2.01- 1.69 (m, 4H), 1.59-1.53 (m, 3H), 1.48-1.33 (m, 15H), 1.24-1.12 (m, 4H), 0.64- 0.60(m, 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, 1-Methyl-1H-pyrazole-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LLINAS-BRUNET, Montse; BORDELEAU , Josee; GODBOUT, Cedrickx; LEBLANC, Melissa; MOREAU, Benoit; O’MEARA, Jeffrey; WO2011/63501; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 25016-20-0, 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. 25016-20-0, name is 1-Methyl-1H-pyrazole-3-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Acid R2a (9.03 mg; 0.072 mmol) is dissolved in DMF (2 mL) and TEA (33.3 muIota 0.072 mmol) and TBTU (23.0 mg; 0.072 mmol) are added and the mixture is stirred for 15 mins. The Boc de-protected macrocyclic amine hydrochloride Ch is dissolved in DMF (1.0 mL) and added to the acid solution and stirred at RT overnight. The resulting solution is filtered through a Millex filter and purified by prep HPLC (ammonium bicarbonate/MeOH). The pure fractions are combined, concentrated, frozen and lyophilized to provide compound 1029.FIA M.S.(electrospray) : 858.3 (M-H)”, 860.2 (M+H)+ Retention time (min): 6.9 min1H NMR (400 MHz,DMSO-d6): delta 10.83 (s, 1H) , 8.93 (s, 1H), 7.90 (d, 1H, J= 9 Hz), 7.79 (d, 1H, J= 7Hz), 7.75 (d, 1H, J= 2.4 Hz), 7.16 (d, 1H, J= 9 Hz), ), 6.61 (s, 1H), 6.57 (d, 1H, J =2.3 Hz), 5.65-5.58 (m 1H), 5.52 (m, 1H), 5.20-5.04 (m, 3H), 4.61- 4.54 (m, 2H), 4.43-4.39 (m, 2H), 4.05-4.00 (m, 2H), 3.89 (d,6H, J = 5.8Hz), 2.67- 2.60 (m, 1H), 2.45 (s, 3H), 2.40-2.29 (m, 2H), 1.97-1.91 (m, 1H), 1.83-1.75 (m, 1H), 1.60-1.49 (m, 3H), 1.43-1.33 (m, 7H), 1.32-1.23 (m, 3H), 0.92-0.84 (m= 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, 1-Methyl-1H-pyrazole-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LLINAS-BRUNET, Montse; BORDELEAU , Josee; GODBOUT, Cedrickx; LEBLANC, Melissa; MOREAU, Benoit; O’MEARA, Jeffrey; WO2011/63501; (2011); 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 25016-20-0 as follows. Quality Control of 1-Methyl-1H-pyrazole-3-carboxylic acid

Compound 1007; (2R.6S, 12Z, 13aS, 14aR, 16aS)-2-{[7-methoxy-8-methyl-2-(propan-2-yloxy)quinolin-4- yl]oxy}-N-[(1-methylcyclopropyl)sulfonyl]-6-{[(1 -methyl- 1 H-pyrazol-3- yl)carbonyl]amino}-5,16-dioxo-1, 2,3,6,7,8,9,10,11,13a,14,15,16,16a- tetradecahydrocyclopropa[e]pyrrolo[1 ,2-a][1 ,4]diazacyclopentadecine-14a(5H)-Ca; Acid R2a (6.6 mg, 0.052 mmol, 1.3 equiv) is dissolved in DMF (0.5 ml_), then TEA (28muIota_, 0.20 mmol, 5.0 equiv) is added followed by TBTU (15.4 mg, 0.048 mmol, 1.2 equiv). The solution is stirred for 15 mins, after which the amine hydrochloride Ca is added in DMF (0.5 mL) and this solution is stirred at RT for 16 h. Water (2 mL) is added to the solution, and then the organic layer is extracted with EtOAc (3×5 mL) and dried over MgS04. The solvent is evaporated and the residue is purified on prep HPLC (MeCN:H20, 0.1% TFA). The pure fractions are combined, concentrated, frozen and lyophilized to provide compound 1007.FIA M.S.(electrospray) : 820.3 (M+H)+ Retention time (min): 5.7 min1H NMR (400 MHz,DMSO-d6): delta 10.83 (s, 1H) , 8.93 (s, 1H), 7.83 (d, 1H, J = 8.8 Hz), 7.79 (d, 1H, J= 7 Hz), 7.77 (d, 1H, J = 2.1 Hz), 7.08 (d, 1H, J = 9 Hz), 6.60 (d, 1H, J = 2.3 Hz), 6.37 (s, 1H), 5.66-5.58 (m, 1H), 5.62 (S, 1H, J = 6.2 Hz), 5.47-5.44 (m, 1H), 5.07 (dd, 1H, J = 9.5, 9.2 Hz), 4.64-4.54 (m, 1H) 4.52 (d, 1H, J = 11.6 Hz), 4.40 (dd, 1H, J = 9.7, 7.1 Hz), 4.02 (dd, 1H, J = 11.8, 3.5 Hz), 3.89 (s, 3H), 3.88 (s, 3H), 2.66-2.57 (m, 1 H) , 2.51 (s, 3H), 2.43 (s, 3H), 2.38-2.29 (m, 2H), 2.02-1.90 (m, 1H), 1.88-1.77 (m, 1H), 1.58 (dd, 1H, J =8.2, 5.1 Hz), 1.52 (dd, 1H, J =9.3, 5.2 Hz), 1.45-1.35 (m, 12H), 1.34-1.20 (m, 4H), 0.93-0.84 (m, 2H).

According to the analysis of related databases, 25016-20-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LLINAS-BRUNET, Montse; BORDELEAU , Josee; GODBOUT, Cedrickx; LEBLANC, Melissa; MOREAU, Benoit; O’MEARA, Jeffrey; WO2011/63501; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

25016-20-0, name is 1-Methyl-1H-pyrazole-3-carboxylic acid, 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. Safety of 1-Methyl-1H-pyrazole-3-carboxylic acid

Examples 213 to 239 General ProcedureThe carboxylic acid R’COOH (0.12 mmol) is treated with a solution of HATU (0.12 mmol) in DMF (0.25 ml) and DIPEA (0.052 ml, ca. 0.3 mmol) is added. The solution is shaken for 10 mins, and is treated with a solution of Intermediate 15 or 16 (0.1 mmol) in DMF (0.2 ml). The resulting solution is shaken for 10 mins and left to stand for 18 h (e.g. at room temperature), and then the DMF is removed in a Genevac vacuum centrifuge. The residue is dissolved in chloroform (0.3 ml), is applied to an SPE cartridge (1 g, aminopropyl) which has been pre-washed with chloroform (6 ml), and is eluted sequentially with chloroform (3 ml) and 10% methanol in ethyl acetate (3 ml). Fractions containing the desired product are concentrated in vacuo in a Genevac vacuum centrifuge, and where necessary the residue is purified by mass directed autoprep HPLC (e.g. acetonitrile/water). Where necessary, the compound(s) is/are dissolved in chloroform, and is/are further purified by loading onto a SPE cartridge (0.5 g, aminopropyl) which has been prewashed with chloroform, eluting with 10% methanol in ethyl acetate.; Example 238 (Synthesis B) N-{[(1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1-methyl-1H-pyrazole-3-carboxamide An example of a specific synthesis (Synthesis B) of Example 238 is as follows:HATU (1.095 g) was dissolved in DMF (6 ml) and an aliquot (0.25 ml) of this solution added to 1-methyl-1H-pyrazole-3-carboxylic acid (0.12 mmol). DIPEA (0.052 ml) was added and the solution shaken for 10 mins. Meanwhile Intermediate 16 (364 mg) was dissolved in DMF (2.4 ml) and an aliquot (0.2 ml) of this solution added. The solution was shaken for 10 min and left to stand for 18 h. DMF was removed in a Genevac vacuum centrifuge and the residue dissolved in chloroform (0.3 ml) and applied to an SPE cartridge (1 g, aminopropyl) pre-washed with chloroform (6 ml). The cartridge was eluted with chloroform (3 ml) and the solvent removed in a Genevac. The residue was dissolved in 50% DMSO in methanol (0.5 ml) and purified by mass directed autoprep HPLC followed by SPE cartridge (0.5 g, Flash NH2) eluting with 10% methanol in ethyl acetate to give Example 238 (20.7 mg). LCMS showed MH+=462; TRET=1.87 min.

The synthetic route of 25016-20-0 has been constantly updated, and we look forward to future research findings.

These common heterocyclic compound, 25016-20-0, name is 1-Methyl-1H-pyrazole-3-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. Recommanded Product: 25016-20-0

Step 1: Preparation ofmethyl 1-methyl-JH-pyrazole-3-carboxylate. To a solution of i-methyl1H-pyrazole-3-carboxylic acid (504 mg, 4 mmol) in MeOH (5 mL) was added SOC12 (1.4 mL, 20 mmol) at 0C. The mixture was stirred at r.t overnight then concentrated under reduced pressure. The residue was dissolved in EtOAc, washed withsatd. aq. NaHCO3and concentrated to afford methyl 1 -methyl-1H-pyrazole-3-carboxylate.LC-MS: m/z 141 (M+H).

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

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. 25016-20-0, name is 1-Methyl-1H-pyrazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., Formula: C5H6N2O2

Example 1652-(4′-(3-((3S,5R)-3,5-Dimethylpiperazin-l-yl)propyl)biphenyl-3-yloxy)-5-fluoro-N-((ls,4s)-4-(l-methyl-lH-pyrazole-3-carboxamido)cyclohexyl)nicotinamide To a suspension of N-((ls,4s)-4-aminocyclohexyl)-2-(4′-(3-((3S,5R)-3,5-dimethylpiperazin-l- yl)propyl)biphenyl-3-yloxy)-5-fluoronicotinamide (150 mg, 0.24 mmol) in acetonitrile (4 mL) was added 1 -methyl- lH-pyrazole-3-carboxylic acid (37 mg, 0.30 mmol) and triethylamine (0.330 mL, 2.37 mmol). 1-Propanephosphonic acid cyclic anhydride, 1.57M solution in THF (0.189 mL, 0.30 mmol) was then added and the mixture stirred at RT for 2 hours. The mixture was evaporated to dryness and the residue dissolved in DCM (100 ml) and washed with saturated NaHCC^aq), brine, dried (MgSC^) and evaporated to give a foam. This was purified by HPLC to give the title compound as a white solid. Yield: 84 mg 1H NMR (400 MHz, CD3OD) delta 8.46 (d, J= 7.5 Hz, IH), 8.12 (d, J= 3.1 Hz, IH), 8.08 – 8.04 (m, IH), 7.58 – 7.56 (m, IH), 7.54 – 7.50 (m, 2H), 7.48 – 7.45 (m, 2H), 7.41 – 7.38 (m, IH), 7.26 – 7.23 (m, 2H), 7.17 – 7.12 (m,lH), 6.65 (d, J= 2.3 Hz, IH), 4.16 – 4.08 (m, IH), 4.00 – 3.90 (m, IH), 3.84 (s, 3H), 3.58 – 3.46 (m, 4H), 2.95 – 2.87 (m, 2H), 2.71 (t, J= 7.6 Hz, 2H), 2.57 (t, J= 12.8 Hz, 2H), 2.05 – 1.94 (m, 2H), 1.91 – 1.77 (m, 6H), 1.74 – 1.62 (m, 2H), 1.33 (d, J= 6.7 Hz, 6H). MS: [M+H]+=668 (calc=668) (MultiMode+)

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.

Adding a certain compound to certain chemical reactions, such as: 25016-20-0, name is 1-Methyl-1H-pyrazole-3-carboxylic acid, 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 25016-20-0, Computed Properties of C5H6N2O2

Acid R2a (13.9 mg; 0.1 10mmol) is dissolved in DMF (2 mL) and TEA (51.2 muIota 0.367 mmol) and TBTU (34.0 mg; 0.1 10 mmol) are added and the mixture is stirred for 15 mins. The Boc de-protected macrocyclic amine hydrochloride Cf is dissolved in DMF (1.0 mL) and added to the acid solution and stirred at RT overnight. The resulting solution is filtered through a Millex filter and purified by prep HPLC (ammonium bicarbonate/MeOH). The pure fractions are combined, concentrated, frozen and lyophilized to provide compound 1003.FIA M.S.(electrospray) : 822.5/ 824.5 (M-H)- , 824.4/ 826.3 (M+H)+Retention time (min): 7.0 min1H NMR (400 MHz,DMSO-d6): delta 10.83 (s, 1 H) , 8.92 (s, 1 H), 7.86 (d, 1 H, J = 8.6 Hz), 7.79 (d, 1 H, J = 5.1 Hz), 7.75 (d, 1 H, J = 2 Hz), 7.29 (d, 1 H, J = 8.6 Hz), 6.57 (s, 1 H), 6.53 (d, 1 H, J = 2 Hz), 5.67- 5.55 (m, 1 H), 5.55- 5.44 (m, 2H), 5.12- 5.00(m, 1 H), 4.62- 4.50 (m, 2H), 4.45- 4.37 (m, 1 H), 4.05- 3.95 (m, 1 H), 3.88 (s, 3H), 2.66 (s, 3H), 2.40- 2.25 (m, 2H), 2.03- 1.87 (m, 1 H), 1.87-1.72 (m, 1 H), 1.60- 1.47(m, 3H), 1.47-1.15 (m, 19H), 0.95- 0.78 (m, 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, 1-Methyl-1H-pyrazole-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.