Category: 31037-02-2

Electric Literature of 31037-02-2,Some common heterocyclic compound, 31037-02-2, name is Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, molecular formula is C7H11N3O2, 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.

The acid chloride reaction solution was synthesized in the same manner as in Example 1.75 g of water, 67 g of pyrazole amine, 42 g of sodium carbonate and 5 g of triethylamine were added to 1000 ml, cooled to 0 to 5 C, and acyl chlorideThe reaction solution was controlled at a temperature of 5 to 10 C. The dropwise addition was completed and the reaction was completed for 1 hour. The reaction was completed, the layers were separated and the organic phase was dissolved to obtain a crude product.Add 200g of methanol heated to 50 C dissolved, cooled to 5 C, precipitated the solid, filtered to give the product as a white solid, yield:82%, content: 95%.

The synthetic route of 31037-02-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Fuding Chemical Co., Ltd.; Liu, Dongwei; Cheng, Lizhong; Chang, Qing; Dong, Hailong; Zhu, Ruiyu; Gu, Junkun; (11 pag.)CN106631896; (2017); A;,
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 31037-02-2 as follows. COA of Formula: C7H11N3O2

Intermediate 32: Ethyl 5-(benzylsulfanyl)-l-methyl-lH-pyrazole-4-carboxylate Dibenzyl disulfide (101.9 g, 413.57 mmol) was added in portions to a solution of ethyl 5- amino-1 -methyl- lH-pyrazole-4-carboxylate (10 g, 59.11 mmol) in MeCN (400 mL) in an atmosphere of nitrogen and at rt. CuCl (293 mg, 7.14 mmol) was added in portions at rt to the reaction mixture and it was stirred at rt for 30 min. 3 -Methyl- 1-nitrobutane (41.5 g, 354.26 mmol) was added to the reaction mixture and the resulting solution was stirred at rt for 30 min and then at 60C for 1 h. The reaction mixture was allowed to reach rt and the solids were filtered off. The filtrate was concentrated under vacuum and the residue was purified by silica gel column chromatography (EtO Ac/petroleum ether, 1 :8) to give the title compound (11.6 g, 71%) as yellow oil. MS m/z 111 [M+H]+

According to the analysis of related databases, 31037-02-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; BRODDEFALK, Johan, Olof; EMTENAeS, Hans, Fredrik; GRANBERG, Kenneth, Lars; LEMURELL, Malin, Anita; PETTERSEN, Daniel, Tor; PLOWRIGHT, Alleyn, Thomas; ULANDER, Lars, Johan, Andreas; (161 pag.)WO2016/177703; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 31037-02-2, 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. 31037-02-2, name is Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 1 Ethyl 4-hydroxy-l-methyl-6-oxo-6,7-dihydro-lH-pyrazolo[3,4- delta]pyridine-5-carboxylate 3O ONaOEt / EtOH Reflux [00192] Sodium ethoxide (95%, 83g, 1.18 moles) was dissolved in 175 mL of absolute ethanol, following the protocol described in J. Heterocyclic Chem. (1978) 15:319 with some modifications. Diethylmalonate 2 (184.6 g, 1.18 moles) was added and stirred at room temperature for 10 minutes. Ethyl 5-amino-l-methylpyrazole-4-carboxylate 1 (5Og, 0.295 moles) was added slowly and the resulting solution refluxed overnight at 100 0C. During the reflux period, an off-white solid began to form. The solution was evaporated to dryness on a rotary evaporator and the residue dissolved in a minimum amount of water. Upon acidification (pH 2) of the aqueous solution with concentrated hydrochloric acid, the resulting precipitate was filtered and recrystallized from acetic acid-water to give 3 as a white solid (~45g , 64%). NMR (trifluoroacetic acid): delta 1.60(t.3H.J=7Hz, CH3 of ester), 4.22(s, 3H, N- CH3), 4.80 (q, 2H, j=7hz, CH2), 8.49 (s, IH, H-3)

The synthetic route of Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; DOTSON, Jennafer; HEFFRON, Tim; OLIVERO, Alan G.; SUTHERLIN, Daniel P.; STABEN, Steven; WANG, Shumei; ZHU, Bing-Yan; CHUCKOWREE, Irina S.; FOLKES, Adrian J.; WAN, Nan Chi; WO2010/59788; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 31037-02-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 31037-02-2 name is Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

EXAMPLE IX.5 This Example illustrates a preparation of ethyl 5-(4,4-difluorobut-3-enylthio)-1-methylpyrazol-4-yl carboxylate (Compound IX.34). Bis-(4,4-difluorobut-3-enyl)disulfide (2.90 g) and tert.butyl nitrite (1.22 g) in acetonitrile (40 cm3) were heated to 60 C. under an atmosphere of nitrogen. To the stirred solution was added dropwise ethyl 5-amino-1-methylpyrazol-4-yl carboxylate (1.00 g) in acetonitrile (10 cm3). On complete addition the reaction solution was heated for 2 hours at 60 C., evaporated under reduced pressure and fractionated by chromatography (silica; hexane:diethyl ether, 5:1 by volume) to give Compound IX.34 (yield 42%). M+ =276; 1 H NMR: delta 1.38(3H,t); 2.20(2H,m); 3.05(2H,t); 3.97(3H,s); 4.25(1H,m); 4.34(2H,q); 7.98(1H,s); (oil).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Zeneca Limited; US5705516; (1998); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 31037-02-2, name is Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, molecular formula is C7H11N3O2, 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 Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate

Carboxylate 62 (20.0 g, 118 mmol) in ethanol (100 mL) was treated with aqueous sodium hydroxide (50 mL, 3 M). The reaction mixture was heated to reflux and allowed to stir for 2 h and the ethanol removed under reduced pressure. The aqueous solution was cooled to 0 C and acidified with HCl (3 M) to pH 5. The white precipitate was collected by filtration and heated neat to 185 C in Kugelrohr oven under vacuum (1 mmHg) to afford titled compound 22 (10.0 g, 87%) as a light brown solid. MP: 73 – 74 C; IR (Diamond Cell, neat): 3395, 3134, 1643, 1556, 1517, 1431, 1344, 1268, 1207, 999, 928, 758, 632 cm-1; 1H NMR (300 MHz, Chloroform-d) delta 7.21 (d, J = 2.0 Hz, 1H), 5.49 (d, J = 2.0 Hz, 1H), 3.62 (s, 3H), 3.50 (br. s, 2H); 13C NMR (75 MHz, Chloroform-d) delta 144.6 (C), 138.2 (CH), 91.2 (CH), 34.3 (CH3); LRMS (ESI+) m/z: 98 (100, [M + H]+), 120 (50, [M + Na]+). This data matched that previously reported. 3

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 31037-02-2, its application will become more common.

Reference:
Article; Katte, Timothy A.; Reekie, Tristan A.; Werry, Eryn L.; Jorgensen, William T.; Boyd, Rochelle; Wong, Erick C.N.; Gulliver, Damien W.; Connor, Mark; Kassiou, Michael; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 330 – 333;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 31037-02-2, 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. 31037-02-2, name is Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

5-Amino-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (5.0 g, 29.6 mmol) was added portionwise to a mixture of tert-butyl nitrite (4.57 g, 44.3 mmol) and copper (II) bromide (7.92 g, 35.5 mmol) in acetonitrile (20 mL). The mixture was heated to 60C for 2 h. The resulting mixture was poured into 6M HCl (200 mL) and extracted with dichloromethane (3 x 250 mL). The combined organics was dried on magnesium sulfate and concentrated in vacuo. The crude material was purified by column chromatography (SiO2, 0% to 50% ethyl acetate in hexanes) to afford 5-bromo-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester as an off-white solid (4.7 g, 68%). 1H NMR (CDCl3) : 7.93 (s, 1H), 4.32 (q, J = 7.2 Hz, 2H), 3.92 (s, 3H), 1.36 (t, J = 7.0 Hz, 3H).

The chemical industry reduces the impact on the environment during synthesis Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BOLIN, David Robert; DE VICENTE FIDALGO, Javier; HERMANN, Johannes Cornelius; TIVITMAHAISOON, Parcharee; YI, Lin; ZAK, Mark; WO2013/189904; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 31037-02-2,Some common heterocyclic compound, 31037-02-2, name is Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, molecular formula is C7H11N3O2, 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.

The acid chloride reaction solution was synthesized in the same manner as in Example 1.75 g of water, 67 g of pyrazole amine, 42 g of sodium carbonate and 5 g of triethylamine were added to 1000 ml, cooled to 0 to 5 C, and acyl chlorideThe reaction solution was controlled at a temperature of 5 to 10 C. The dropwise addition was completed and the reaction was completed for 1 hour. The reaction was completed, the layers were separated and the organic phase was dissolved to obtain a crude product.Add 200g of methanol heated to 50 C dissolved, cooled to 5 C, precipitated the solid, filtered to give the product as a white solid, yield:82%, content: 95%.

The synthetic route of 31037-02-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Fuding Chemical Co., Ltd.; Liu, Dongwei; Cheng, Lizhong; Chang, Qing; Dong, Hailong; Zhu, Ruiyu; Gu, Junkun; (11 pag.)CN106631896; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 31037-02-2, name is Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, 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. category: pyrazoles-derivatives

A solution of ethyl 5-amino-1-methyl-4-pyrazole carboxylate (42.2 g, 0.25 mol) in THF is treated with NaH (60% in mineral oil, 25.2 g, 0.75 mol), stirred for 30 min, treated with ethyl 3-methoxy-3-[(trifluoromethyl)phenyl]-2-propenoate (65.5 g, 0.25 mol), heated at reflux temperature for 36 h, cooled to 0 C., acidified to pH 5 with aqueous HCl and extracted with EtOAc. The extracts are combined, washed with brine, dried over Na2SO4 and concentrated in vacuo. The resultant off-white solid residue is triturated with hexanes to give a white solid. The solid is dissolved in phosphorus oxychloride (750 mL) and heated to reflux temperature for 2 h, cooled to room temperature and concentrated. This concentrate is dissolved in EtOAc, cooled to 0 C., and neutralized with aqueous Na2CO3. The organic phase is separated, washed with brine, dried over Na2SO4 and concentrated. This resultant residue is chromatographed on silica gel (3:1 hexanes:EtOAc) to afford the title compound as a white solid 65% (68% yield), characterized by H-NMR and mass spectral analyses.

The synthetic route of Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; US2004/24008; (2004); 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 31037-02-2 as follows. Recommanded Product: Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate

Intermediate 32: Ethyl 5-(benzylsulfanyl)-l-methyl-lH-pyrazole-4-carboxylate Dibenzyl disulfide (101.9 g, 413.57 mmol) was added in portions to a solution of ethyl 5- amino-1 -methyl- lH-pyrazole-4-carboxylate (10 g, 59.11 mmol) in MeCN (400 mL) in an atmosphere of nitrogen and at rt. CuCl (293 mg, 7.14 mmol) was added in portions at rt to the reaction mixture and it was stirred at rt for 30 min. 3 -Methyl- 1-nitrobutane (41.5 g, 354.26 mmol) was added to the reaction mixture and the resulting solution was stirred at rt for 30 min and then at 60C for 1 h. The reaction mixture was allowed to reach rt and the solids were filtered off. The filtrate was concentrated under vacuum and the residue was purified by silica gel column chromatography (EtO Ac/petroleum ether, 1 :8) to give the title compound (11.6 g, 71%) as yellow oil. MS m/z 111 [M+H]+

According to the analysis of related databases, 31037-02-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; BRODDEFALK, Johan, Olof; EMTENAeS, Hans, Fredrik; GRANBERG, Kenneth, Lars; LEMURELL, Malin, Anita; PETTERSEN, Daniel, Tor; PLOWRIGHT, Alleyn, Thomas; ULANDER, Lars, Johan, Andreas; (161 pag.)WO2016/177703; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 31037-02-2, The chemical industry reduces the impact on the environment during synthesis 31037-02-2, name is Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, I believe this compound will play a more active role in future production and life.

To a dry flask under nitrogen at 0C charged with 60 wt.% NaH (296 mg, 7.39 mmol) and ethyl 5-amino-l-methyl-lH-pyrazole-4-carboxylate (500 mg, 2.96 mmol) was added 10 mL THF. (0437) The mixture was stirred for 10 minutes at which point CS2 (1.782 mL, 29.6 mmol) was added by syringe. The mixture was allowed warm to room temperature then heated to 40C and stirred for 3H. After cooling the flask to 0C and iodine was added portion wise over 10 minutes. The mixture was stirred for another hour at 0C then 30 mL diethyl ether was added and the precipitate was filtered off. The filtrate was washed 3x with IN HC1, lx with brine and the organic portion was dried over sodium sulfate and the solvent removed yielding a reddish black solid. The crude product was purified by flash (0-30% EA in Hex) yielding the titled compound as a yellow solid (460mg, 2.178 mmol, 73.7 % yield). M+H found 212.0 XH NMR (400 MHz, CDCI3) delta 7.81 (s, 1H), 4.25 – 4.44 (m, 2H), 3.80 (s, 3H), 1.30 – 1.44 (m, 3H)

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, Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; LARSEN, Scott D.; HUDDLE, Brandt C.; YANG, Kun; BUCKANOVICH, Ronald; HURLEY, Thomas; (127 pag.)WO2017/223086; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics