Category: 16034-46-1

Application of 16034-46-1, 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. 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 1-methyl-1H-pyrazole-5-carboxylic acid (compound 4A, 1.99 g, 15.8 mmol), DIEA (5.95 g, 46.0 mmol) in CH2Cl2 (20 mL) was added EDCI (5.04 g, 26.3 mmol) and DMAP (1.93 g, 15.8 mmol) at -5 C., the mixture was stirred at -5 C. for 30 min under N2. Then 2-methyl-4-nitroaniline (compound 15, 2.00 g, 13.1 mmol) was added, the mixture was stirred at -5 C. for 30 min, then warmed to 25 C., stirred for 11 hrs. TLC (petroleum ether:ethyl acetate=1:1, Rf=0.55) showed starting material consumed completely. The mixture was concentrated in vacuum to give light yellow oil. The oil was purified by silica gel column chromatograph (petroleum ether:ethyl acetate=100:0 to 50:50) to give 1-methyl-N-(2-methyl-4-nitrophenyl)-1H-pyrazole-5-carboxamide (compound 16, 2.60 g, 76% yield) as light yellow solid.

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

Reference:
Patent; Kyn Therapeutics; Castro, Alfredo C.; Evans, Catherine Anne; (108 pag.)US2019/55218; (2019); 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. 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 16034-46-1

To a solution of 1 -methyl- lH-pyrazole-5-carboxylic acid (2 g, 15.86 mmol) in tetrahydrofuran (50 mL) was added L1AIH4 (720 mg, 18.97 mmol) in portions at 0 C under an inert atmosphere of nitrogen. The reaction was stirred for 2 hours at room temperature then quenched by the addition of water (2 mL). The mixture was dried over by anhydrous sodium sulfate and the solids were filtered out. The filtrates were concentrated under reduced pressure to afford (1 -methyl- lH-pyrazol- 5-yl)methanol as colorless oil (1.2 g, 67 ). (ES, m/z) [M+H]+ 113.0 *H NMR (300 MHz, CDC13) delta 7.36 (d, 7 = 1.8 Hz, 1H), 6.18 (d, 7 = 1.8 Hz, 1H), 4.66 (s, 2H), 3.88 (s, 3H)

The synthetic route of 16034-46-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOENERGENIX; MCCALL, John; KELLY, Robert, C.; ROMERO, Donna, L.; WO2014/66795; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 16034-46-1, name is 1-Methyl-1H-pyrazole-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. Recommanded Product: 1-Methyl-1H-pyrazole-5-carboxylic acid

To a solution of 1-methyl-1H-pyrazole-5-carboxylic acid (compound 4A, 4.58 g, 36.3 mmol), DIEA (13.7 g, 106 mmol) in CH2Cl2 (30 mL) was added EDCI (11.6 g, 60.5 mmol) and DMAP (4.44 g, 36.3 mmol) at -5 C., the mixture was stirred at -5 C. for 30 min. Then methyl 4-amino-3-methylbenzoate (compound 11, 5.00 g, 30.3 mmol) was added, stirred at -5 C. for 30 min. The mixture was warmed to 25 C., stirred for 11 hrs. TLC (petroleum ether:ethyl acetate=1:1, Rf=0.52) showed starting material consumed completely. The mixture was concentrated in vacuum to give light yellow oil. The oil was purified by silica gel column chromatography (petroleum ether:ethyl acetate=90:10 to 50:50) to give methyl 3-methyl-4-(1-methyl-1H-pyrazole-5-carboxamido)benzoate (compound 12, 5.70 g, 69% yield) as light yellow solid.

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

Reference:
Patent; Kyn Therapeutics; Castro, Alfredo C.; Evans, Catherine Anne; (108 pag.)US2019/55218; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

16034-46-1, name is 1-Methyl-1H-pyrazole-5-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. COA of Formula: C5H6N2O2

1) N-methoxy-N,1-dimethyl-1H-pyrazol-5-carboxamide N,O-dimethylhydroxylamine hydrochloride (1.30 g) was added to an N,N-dimethylformamide (32 mL) solution that contained 1-methyl-1H-pyrazol-5-carboxylic acid (1.21 g), O-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (4.38 g) and diisopropylethylamine (3.34 mL) at a room temperature, and the obtained solution was then stirred for 2 hours. Thereafter, water was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was washed with water and a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, chloroform_methanol=100:0 to 95:5), so as to obtain the title compound (1.03 g) in the form of a yellow oily substance. 1H NMR (200 MHz, CHLOROFORM-d) delta ppm 3.36 (s, 3H) 3.66 (s, 3H) 4.13 (s, 3H) 6.77 (d, J=2.20 Hz, 1H) 7.48 (d, J=2.20 Hz, 1H); MS (ESI pos.) m/z: 170 [M+H]+

The synthetic route of 16034-46-1 has been constantly updated, and we look forward to future research findings.

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; Amada, Hideaki; Urabe, Hiroki; Nishikawa, Rie; Kashiwa ASHIWA, Shuhei; US2013/137865; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 16034-46-1,Some common heterocyclic compound, 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, molecular formula is C5H6N2O2, 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 tert-butyl {4-methyl-2-[3-(methylsulfonyl)benzyl]-1,3-thiazol-5-yl}carbamate (300 mg, 0.78 mmol) obtained in Example 233-F) in ethanol (2 mL) was added dropwise concentrated hydrochloric acid (0.600 mL) at room temperature, and the mixture was stirred at 50C for 1 hr. The reaction mixture was cooled to 0C, neutralized with 8N aqueous sodium hydroxide solution, adjusted to pH 10-11 with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was dissolved in DMA (3 mL), and 1-methyl-1H-pyrazole-5-carboxylic acid (118 mg, 0.94 mmol), HATU (356 g, 0.94 mmol) and DIEA (0.068 mL, 0.39 mmol) were added at room temperature. The reaction mixture was stirred at 60C for 2 hr, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: hexane-ethyl acetate (1:4-0:1)] and basic silica gel column chromatography [eluent: hexane-ethyl acetate (1:9-0:1)], and crystallized from ethyl acetate-hexane to give the title compound (159 mg) as white crystals (yield 52%). MS (ESI+) : [M+H]+ 391. 1H NMR (300 MHz, DMSO-d6) delta 2.31 (3H, s), 3.31 (3H, s), 4.04 (3H, s), 4.37 (2H, s), 7.06 (1H, d, J = 1.9 Hz), 7.53 (1H, d, J = 1.9 Hz), 7.59-7.74 (2H, m), 7.80-7.87 (1H, m), 7.91 (1H, brs), 10.52 (1H, s).

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2530078; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 16034-46-1,Some common heterocyclic compound, 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, molecular formula is C5H6N2O2, 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 tert-butyl {4-methyl-2-[2-(trifluoromethyl)benzyl]-1,3-thiazol-5-yl}carbamate (400 mg, 1.07 mmol) obtained in Example 209-D) in ethanol (10 mL) was added dropwise concentrated hydrochloric acid (4.8 mL) at room temperature, and the mixture was stirred at 50C for 1.5 hr. The reaction mixture was cooled to room temperature, neutralized with 8M aqueous sodium hydroxide solution, adjusted to pH 10-11 with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was dissolved in DMA (10 mL), and 1-methyl-1H-pyrazole-5-carboxylic acid (161 mg, 1.28 mmol), HATU (487 mg, 1.28 mmol) and DIEA (0.0884 mL, 0.535 mmol) were added at room temperature. The reaction mixture was stirred at 80C overnight. After cooling to room temperature, saturated aqueous sodium hydrogen carbonate solution was added and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: hexane-ethyl acetate (13:7-7:13)] and basic silica gel column chromatography [eluent: hexane-ethyl acetate (7:3-1:1)], and crystallized from ethyl acetate-hexane to give the title compound (107 mg) as white crystals (yield 26%). MS (ESI+): [M+H]+ 381. 1H NMR (300 MHz, DMSO-d6) delta 2.30 (3H, s), 4.03 (3H, s), 4.39 (2H, s), 7.05 (1H, d, J = 2.3 Hz), 7.51-7.62 (3H, m), 7.69 (1H, d, J = 7.5 Hz), 7.71-7.83 (1H, m), 10.50 (1H, s).

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2530078; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, molecular formula is C5H6N2O2, 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. Safety of 1-Methyl-1H-pyrazole-5-carboxylic acid

42-1 : 1 -Methyl-N-4-[rel-(4aS,5aS)-5a-methyl-4-oxo-3-(phenylamino)-1 ,4,4a,5,5a,6- hexahydrocyclopropa[f]indol-2-yl]pyridin-2-yl-1 H-pyrazole-5-carboxamide A solution of 1 -methyl-1 H-pyrazole-5-carboxylic acid (1 10 mg, 871 muiotaetaomicronIota) and HATU (331 mg, 871 muiotaetaomicronIota) in DMA (3 mL) was added to a mixture of rel-(4aR,5aR)-2-(2-Aminopyridin- 4-yl)-3-anilino-5a-methyl-4a,5,5a,6-tetrahydrocyclopropa[f]indol-4(1 H)-one (26; 100 mg, 290 muiotaetaomicronIota) and DIPEA (152 muIota_, 871 muiotaetaomicronIota) in DMA (3 mL) and stirred for 16 h at 50. The mixture was concentrated, DCM added and washed with water and dried over sodium sulfate. After filtration and concentration the residue was purified by Biotage (SNAP NH 28 g, EtOH:DCM) to give the title compound (91 mg, 69%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16034-46-1, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; GRAHAM, Keith; KLAR, Ulrich; BRIEM, Hans; SIEMEISTER, Gerhard; MOeNNING, Ursula; (145 pag.)WO2017/21348; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 16034-46-1,Some common heterocyclic compound, 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, molecular formula is C5H6N2O2, 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.

A 100 mL round bottom flask was charged with a solution of 2-methylpyrazole-3- carboxylic acid (0.2662 g, 2.1107 mmol), EDC HCL (0.5634 g, 2.8782 mmol) and HOBt (0.389 g, 2.8782 mmol) in DMF (5 mL) and the reaction mixture stirred for 5 min at rt then N,N-diisopropylethylamine (0.7440 g, 5.7565 mmol) was added and the mixture stirred for 5 min. Then was added a solution of tert-butyl 5-[[3-(3-aminophenyl)-1,2,4-thiadiazol-5-yl]-tert- butoxycarbonyl-amino]-4-chloro-indazole-1-carboxylate (1.042 g, 1.9188 mmol) in DMF (5mL) and the solution stirred at room temperature for 24 h. Then, solvents were removed under vacuum and the resulting residue was purified by silica gel chromatography (40 g column, HP 15-40 uM 60 A flash cartridge from Silicycle) eluting with 0 to 50% hexanes/EtOAc to yield the title compound (0.717 g, 57.386% yield) as a light yellow foam.

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

Reference:
Patent; LYCERA CORPORATION; AICHER, Thomas, D.; PADILLA, Fernando; SKALITZKY, Donald, J.; TOOGOOD, Peter, L.; VANHUIS, Chad, A.; (172 pag.)WO2018/39539; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 16034-46-1,Some common heterocyclic compound, 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, molecular formula is C5H6N2O2, 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 1-methyl-1H-pyrazole-5-carboxylic acid (compound 4A, 4.07 g, 32.2 mmol), DIEA (12.2 g, 94.1 mmol) in CH2Cl2 (30 mL) was added EDCI (10.3 g, 53.7 mmol) and DMAP (3.94 g, 32.2 mmol) at -5 C., the mixture was stirred at -5 C. for 30 min under N2. Then 4-bromo-2-methylaniline (compound 7, 5.00 g, 26.9 mmol) was added, the mixture was stirred at -5 C. for 30 min, then warmed to 25 C., stirred for 11 hrs. TLC (petroleum ether:ethyl acetate=1:1, Rf=0.27) showed one new point formed. The mixture was concentrated in vacuum to give light yellow oil. The oil was purified by silica gel column chromatography (petroleum ether: ethyl acetate=80:20 to 50:50) to give N-(4-bromo-2-methylphenyl)-1-methyl-1H-pyrazole-5-carboxamide (compound 8, 6.40 g, 81% yield) as light yellow solid. 1H NMR (400 MHz, CDCl3) delta delta ppm 7.72 (d, J=8.2 Hz, 1H), 7.47-7.58 (m, 2H), 7.33-7.41 (m, 2H), 6.64 (s, 1H), 4.20 (s, 3H), 2.28 (s, 3H); ES-LCMS m/z 294.1 [M+H]+.

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

Reference:
Patent; Kyn Therapeutics; Castro, Alfredo C.; Evans, Catherine Anne; (108 pag.)US2019/55218; (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. 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, A new synthetic method of this compound is introduced below., HPLC of Formula: C5H6N2O2

To a solution of i-methyl-I H-pyrazole-5-carboxylic acid (5.28 g, 41.9 mmol) in dichloromethane (55 ml) was added oxalyl chloride (9.14 ml, 104.8 mmol) followed by 3 drops of dimethylformamide. The reaction was stirred at room temperature for 18 hours before concentration in vacuo. The residue was dissolved in acetonitrile (42 ml) and added dropwise to a cooled solution of 3- (2-chloro-5-methoxyphenyl)pyridine-2,6-diamine (preparation 1 , 9.5 g, 38 mmol) and lutidine (6.6 ml, 57.1 mmol) in acetonitrile (650 ml). The reaction was allowed to warm to room temperature and stirred under nitrogen for 2 hours. The reaction was quenched by the addition of water (300 ml) and concentrated to low volume in vacuo. The aqueous residue was washed with dichloromethane (2×300 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with ethylacetate: heptane 1 :4 to furnish a solid. This was recrystallised from toluene (100 ml) to afford 6.7 g of the title product. LCMS Rt=1.88 min MS m/z 358 [MH]+1HNMR (alphafe-DMSO): 3.75 (s, 3H), 4.05 (s, 3H), 5.3 (br s, 2H), 6.9 (m, 1 H), 6.95 (m, 1 H), 7.2 (m, 1 H), 7.3 (m, 1 H), 7.35 (m, 1 H), 7.45 (m, 1 H), 7.5 (m, 1 H), 10.3 (br s, 1 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; PFIZER LIMITED; WO2008/135826; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics