Category: 632365-54-9

Electric Literature of 632365-54-9, 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. 632365-54-9, name is Methyl 5-amino-1H-pyrazole-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

With stirring, a mixture of 10 g (0.037 mol) of dimethyl(2-chloro-4-cyanophenyl)malonate, 5.2 g (0.037 mol) of methyl 5-amino-1H-pyrazole-3-carboxylate and 7.6 g (0.041 mol) of tri-n-butyl-amine was heated at 180 C. for 6 hours. The methanol released during the reaction was continuously distilled off. The reaction mixture was then concentrated under reduced pressure. This gave 12.8 g (100% of theory) of methyl 5,7-dihydroxy-6-(2-chloro-4-cyanophenyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate. The product was used for further syntheses without additional purification.

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

Reference:
Patent; Gebauer, Olaf; Gayer, Herbert; Heinemann, Ulrich; Herrmann, Stefan; Hillebrand, Stefan; Elbe, Hans-Ludwig; Ebbert, Ronald; Wachendorff-Neumann, Ulrike; Dahmen, Peter; Kuck, Karl-Heinz; US2005/187224; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 632365-54-9, 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 632365-54-9 as follows.

Step d: To a solution of methyl 5-amino-1 H-pyrazole-3-carboxylate (75 mg; 0.53 mmol) in DMF (2 mL) was added the 2-bromo-2-cyclohexyl-1-(4-fluorophenyl)ethanone ( 170 mg; 0.58 mmol) followed by potassium carbonate (263 mg; 2.66 mmol) and the reaction mixture was stirred at 75C. After 2 hours water (25 mL) was added and the aqueous layer was extracted with EtOAc (3 x 30 mL). The combined organics were washed with brine (25 mL), dried (MgS04) and concentrated to leave a brown oil (89 mg). The residue was redissolved in EtOH ( 2 mL) and 2M sulphuric acid (0.5 mL) was added and the reaction mixture was stirred at 70 C. After 2 hours NaHC03 (25 ml) was added and the aqueous layer was extracted with EtOAc (3 x 30 mL). The combined organics were washed with brine (25 mL), dried (MgS04) and concentrated to leave a brown oil (75 mg). Purification by reverse phase LCMS: Acetonitrile/water (0.1 % formic acid) afforded methyl 3-cyclohexyl-2-(4-fluorophenyl)- 1 H-imidazo[1 ,2-b]pyrazole-6-carboxylate (i) (8.5 mg) as an amorphous white solid. ESI-MS m/z calculated for [M+H]+: 342.16; found: 342.09.

According to the analysis of related databases, 632365-54-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOTA SCIENTIFIC MANAGEMENT PTY LTD; FREY, Barbara; HUFTON, Richard; HARDING, Michael; DRAFFAN, Alistair George; WO2013/36994; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 632365-54-9,Some common heterocyclic compound, 632365-54-9, name is Methyl 5-amino-1H-pyrazole-3-carboxylate, molecular formula is C5H7N3O2, 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 1-15d (450 mg, 1.50 mmol) in EtOH (30 mL) was added methyl 5-amino- 1H-pyrazole-3-carboxylate (450 mg, 1.90 mmol) at rt. The reaction mixture was heated at 85 C for 4 h, then concentrated under reduced pressure. The afforded crude was purified by column chromatography on silica gel, eluted with 20% ethyl acetate / pet ether which gave the title compound (300 mg) as a solid with 65% LCMS purity.MS (ES+) m/z 372.33 [M+H]+. The compound was used in next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 5-amino-1H-pyrazole-3-carboxylate, its application will become more common.

Reference:
Patent; MEDIVIR AKTIEBOLAG; ERSMARK, Karolina; KARLSTROeM, Sofia; KLASSON, Bjoern; LUNDGREN, Stina; ROSENQUIST, Asa; SALVADOR ODEN, Lourdes; (155 pag.)WO2018/226150; (2018); 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. 632365-54-9, name is Methyl 5-amino-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C5H7N3O2

To an ice cold suspension of 0.92 g (23 mmol) of sodium hydride (NaH 60% dispersion in mineral oil) (previously washed with hexane and dried under vacuum) in 25 mL of 1,2- dimethoxyethane (DME) was added 0.9 g (5.76 mmol) of [METHYL CYCLOHEXYLACETATE,] and the resulting mixture was stirred at [0 C] for 20 min. Then 1.2 g (8.56 mmol) [OF ETHYL 2-FUROATE] was added, and the reaction mixture was heated at reflux overnight. The mixture was then cooled to [0C,] quenched by the addition of 1 M [HC1] solution to pH=3, and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated to give a brown oil which was chromatographed on silica gel [(BIOTAGE ;] 10% hexane in dichloromethane) to afford 1.1 g (76% yield) of desired 2-cyclohexyl-3-furan-2-yl-3- [OXO-PROPIONIC ACID METHYL ESTER] as indicated by 1H NMR. A mixture of 1.1 g (4.4 mmol) [OF 2-CYCLOHEXYL-3-FURAN-2-YL-3-OXO-P7 OPIONIC ACID] [METHYL ESTER,] 0.592 g (4.2 mmol) of 5-amino-1H-pyrazole-3-carboxylic acid methyl ester, 76 mg (0.4 mmol, 10 mol%) of p-toluenesulfonic acid monohydrate (PTSA), and 50 mL of chlorobenzene was heated at 120 [C] overnight. The reaction mixture was then concentrated to a residue which was chromatographed on silica gel (7% methanol in dichloromethane) to afford 0.46 g (32% yield) of desired 6-cyclohexyl-5-furan-2-yl-7-oxo-4,7-dihydro- pyrazolo[1,5-a]pyrimidine-2-carboxylic acid methyl ester as indicated [BY IH] NMR; LC-MS- calcd for [C18HL9N304] [[M++H] +] : 342.14, found: 342.3. Conversion of 6-cyclohexyl-5-furan-2-yl-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine- 2-carboxylic acid methyl ester to 6-cyclohexyl-5-furan-2-yl-7-oxo-4,7-dihydro-pyrazolo[1,5- [AJPYYIMIDINE-2-CARBOXYLIC ACID] (595) was accomplished via the well known LiOH saponification protocol where the yield was 77%. [LC-MS-CALCD] for [CI7HI7N304] [M++H]+: 328.13, found : 328. 1. 1H NMR [(DMSO-D6)] [8] 8.06-8. 05 (d, J= 2 Hz, 1H), 6.99-6. 98 (d, J= 3.6 Hz, 1H), 6.80-6. 78 (d [OF D,] J= 3.6 Hz, J= 2 Hz, [1H),] 6.39 (s, [1H),] 2.79-2. 71 [(M,] 1H), 2.25-2. 16 [(M,] 2H), 1.77-1. 75 [(M,] [2H),] 1.66-1. 65 [(M,] 1H), 1.59-1. 55 [(M,] 2H), 1.25-1. 20 [(M,] 3H). Note that the same synthetic scheme was carried out for [3-FLUORO-BENZOIC ACID METHYL] ester as depicted above to afford [6-CYCLOHEXYL-5-(3-FLUORO-PHENYL)-7-OXO-4, 7-DISLYDRO-] pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (598); the cyclization yield was slightly improved (54%).

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; NEOGENESIS PHARMACEUTICALS, INC.; WO2003/101993; (2003); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

632365-54-9, name is Methyl 5-amino-1H-pyrazole-3-carboxylate, 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. Product Details of 632365-54-9

5-Amino-3-pyrazolcarboxylic acid methyl ester (16.91 g, 119.8 mmol) is dissolved in ethanol (2.4 L) and hydrochloric acid (37%, 12.5 mL, 150 mmol) is added. Then, a solution of 2-bromo-malonealdehyde (18.9 g, 125.2 mmol) is dissolved in ethanol (1.4 L) and is quickly added in a drop wise manner at RT. After 30 min, a precipitation is observed; after 6 hours the precipitate is removed and washed with 50 ml ethanol and thereafter with 50 ml diethyl ether. Here, 4.19 g of the clean product are isolated. After evaporation of the filtrate and crystallisation, additional 1.43 g product are obtained to yield 6-Bromo-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid methyl ester (5.62 g, 18.3% d. Th.). In case of a smaller scale reaction with only 1 g of the starting amine 5-amino-3-pyrazolcarboxylic acid methyl ester, the yield is much better e.g. 68%.

The synthetic route of 632365-54-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERZ PHARMA GMBH & CO. KGAA; US2008/32998; (2008); 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 632365-54-9 as follows. Recommanded Product: 632365-54-9

To a refluxing mixture of 7.0 g (175 mmol) of sodium hydride (NaH 60% dispersion in mineral oil) and 10.45 g (88.5 mmol) [OF DIETHYL CARBO7LATE (CO (OETJ2)] in 100 mL of toluene was added dropwise via an addition funnel a mixture of 10 g [(44. 3] mmol) [OF 1- (4-BENZYLOXY-] [PHENYL)-ETHANO7LE] in 20 mL of toluene, and the resulting mixture was heated at reflux under argon for 1 h. The reaction mixture was then cooled to [0C,] quenched by the addition of 40 mL of acetic acid, during which time a yellow precipitate formed, and it dissolved upon subsequent addition of water. The separated organic layer was washed with saturated sodium bicarbonate solution, water and brine, dried over sodium sulfate and concentrated to give a residue which was chromatographed on silica gel (10% hexane in dichloromethane) to afford 9.2 g (70% yield) of desired [3-(4-BENZYLOXY-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER] as indicated by 1H NMR. To a solution of 2 g (6.7 mmol) of 3-(4-benzyloxy-pyenyl)-3-oxo-propionic acid ethyl ester in 12 mL of ethanol (heated slightly for complete dissolution) was added dropwise 7 mL (7 mmol) [OF POTASSIUFN T-BUTOXIDE (KOTBU 1 MSOLUTION IN T-BUTANOL),] during which time a precipitate formed. The reaction mixture was stirred at rt for 20 min, then diethyl ether was added and the precipitate was collected by filtration, washed with ether and dried to afford 2.2 g (98% yield) of desired [3-(4-BENZYLOXY-PHE7LYL)-3-OXO-PROPIONIC ACID ETHYL ESTER POTASSIUM] salt as indicated by 1H NMR. A mixture 100 mg (0.3 mmol) of 3-(4-benzyloxy-phenyl)-3-oxo-propionic acid ethyl ester potassium salt, 86 mg (0.45 mmol) of 2-cyclohexylethyl bromide, and 17 mg (0.1 mmol) of potassium iodide (KI) in 1 mL [OF DIMETHYLFONNAMIDE (DMF)] in a 4 mL vial was shaken in a sand bath at [80 C] overnight. The mixture was then concentrated to give a residue which was purified via reverse-phase chromatography (Gilson) to afford (after lyophilization) 85 mg (70% yield) of 2- (4-benzyloxy-benzoyl)-4-cyclohexyl-butyric acid ethyl ester as a solid as indicated by LC-MS-calcd for [C26H3202 [M++H] +] : 409.23, found: 409.2. A mixture of 71 mg (0.171 mmol) [OF 2-(4-BENZYLOXY-BE7LZOYL)-4-CYCLOHEXYL-BUTYRIC ACID] ethyl ester, 24 mg (0.171 mmol) of [5-AMINO-1H-PYRAZOLE-3-CARBOXYLIC ACID METHYL ESTER,] 7 mg (20 [MOL%)] [OF P-TOLUEYLESULFOFZIC ACID MONOHYDRATE (PTSA),] and 3 mL of chlorobenzene was heated at [120 C] overnight. The reaction mixture was then concentrated to a residue which was purified via reverse-phase chromatography (Gilson) to afford (after lyophilization) desired 5-(4-benzyloxy-phenyl)-6-(2-cyclohexyl-ethyl)-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine- 2-carboxylic acid methyl ester as a solid as indicated by LC-MS-calcd for [C29H3LN304] [[M +H] +] : 486.23, found: 486.2. This material was then converted to 5-(4-benzyloxy-phenyl)- 6-(2-cyclohexyl-ethyl)-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (559) via the well known LiOH saponification protocol (10% yield over 2 steps); LC-MS-calcd for [C2SH29N304] [[M++H] +] : 472.22, found: 472.2. Note that the same synthetic sequence was carried out from the commercially available [3-FURAN-3-YL-3-OXO-PROPIONIC ACID ETHYL ESTER] as depicted above to give [6- (2-CYCLOHEXYL-ETHYL)-] 5-furan-3-yl-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (612).

According to the analysis of related databases, 632365-54-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEOGENESIS PHARMACEUTICALS, INC.; WO2003/101993; (2003); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 632365-54-9, 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. 632365-54-9, name is Methyl 5-amino-1H-pyrazole-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Under argon, lithium borohydride (2M in THF, 84.2 ml) was added dropwise to a stirred solution of methyl 5-aminopyrazole-3-carboxylate (9.5 g) in tetrahydrofuran (300 ml). The resultant mixture was heated to reflux for 16 hours. The mixture was cooled and methanol was added dropwise to quench residual reducing agent. The mixture was evaporated. Methanol (200 ml) was added to the residue and insoluble salts were removed by filtration. The filtrate was evaporated and the residue was purified by column chromatography on silica using a solvent gradient of 9:1 to 4:1 of methylene chloride and methanol as eluent. There was thus obtained 3-amino-5-hydroxymethyl-li?-pyrazole (5.6 g) 1H NMR: (DMSOd6) 4.27 (s, 2H)5 4.3-5.2 (2 br s, 3H), 5.29 (s, IH).

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

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. 632365-54-9, name is Methyl 5-amino-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 632365-54-9

With stirring, a mixture of 10 g (0.046 mol) of diethyl sec-butylmalonate, 6.5 g (0.046 mol) of methyl 5-amino-1H-pyrazole-3-carboxylate and 9.4 g (0.051 mol) of tri-n-butylamine was heated at 180 C. for 6 hours. During this time, the ethanol released during the reaction was continuously distilled off. The reaction mixture was then concentred under reduced pressure. This gave 12.2 g (100% of theory) of methyl 5,7-dihydroxy-6-(sec-butyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylate. The product was used for further syntheses without additional purification.

The synthetic route of 632365-54-9 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. 632365-54-9, name is Methyl 5-amino-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., name: Methyl 5-amino-1H-pyrazole-3-carboxylate

[00126] delta-Amino-S-pyrazolcarboxylic acid methyl ester (16.91 g, 119.8 mmol) is dissolved in ethanol (2.4 L) and hydrochloric acid (37%, 12.5 ml_, 150 mmol) is added. Then, a solution of 2-bromo-malonaldehyde (18.9 g, 125.2 mmol) in ethanol (1.4 L) and is quickly added in a dropwise manner at RT. After 30 min, a precipitation is observed; after 6 hours the precipitate is filtered and washed with 50 mL ethanol and thereafter with 50 mL diethyl ether to give 4.19 g of 6-bromo-pyrazolo[1 ,5a]pyrimidine-2-carboxylic acid methyl ester. After evaporation of the filtrate and crystallisation, an additional 1.43 g of product is obtained. Totally 5.62 g (18.3 %).

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: 632365-54-9, name is Methyl 5-amino-1H-pyrazole-3-carboxylate, 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 632365-54-9, COA of Formula: C5H7N3O2

Step C. Methyl 3-amino-lH-pyrazole 5-carboxylate (325 mg, 2.3 mmol) and methyl acetoacetate (330mg, 2.3 mmol) in methanol (10 mL) were heated to reflux for 2h and cooled down. The resulting precipitate was collected to give white solid product 7-Methyl-pyrazolo[l,5-a]pyrimidine-2,5-dicarboxylic acid dimethyl ester (356 mg, yield 62%). MS (M + H): 250.

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, Methyl 5-amino-1H-pyrazole-3-carboxylate, other downstream synthetic routes, hurry up and to see.