Category: 42098-25-9

Reference of 42098-25-9, These common heterocyclic compound, 42098-25-9, name is 5-Chloro-1-methyl-4-nitro-1H-pyrazole, 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.

tert-Butyl 8-(1-methyl-4-nitro-1H-pyrazol-5-yl)-2,8-diazaspiro[4.5]decane-2-carboxylate A mixture of 5-chloro-1-methyl-4-nitro-1H-pyrazole from Example 1 (150 mg, 0.93 mmol), tert-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (244 mg, 1.02 mmol) and DIPEA (1 mL) in EtOH (3 mL) was heated at 130 C. in a microwave for 2 hr. The solvent was removed under reduced pressure and the crude product was purified via silica gel column chromatography (50% EtOAc/isohexane) to give tert-butyl 8-(1-methyl-4-nitro-1H-pyrazol-5-yl)-2,8-diazaspiro[4.5]decane-2-carboxylate as a yellow oil (245 mg, 72%). 1H NMR (400 MHz, CDCl3) delta 8.02 (s, 1H), 3.76 (s, 3H), 3.49-3.39 (m, 2H), 3.30-3.00 (m, 6H), 1.90-1.60 (m, 6H), 1.55 (s, 9H).

Statistics shows that 5-Chloro-1-methyl-4-nitro-1H-pyrazole is playing an increasingly important role. we look forward to future research findings about 42098-25-9.

Reference:
Patent; GENENTECH, INC.; Hodges, Alastair James; Matteucci, Mizio; Sharpe, Andrew; Sun, Minghua; Wang, Xiaojing; Tsui, Vickie H.; US2013/79321; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 42098-25-9, 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. 42098-25-9, name is 5-Chloro-1-methyl-4-nitro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step C. tert-Butyl [1-(1-methyl-4-nitro-1H-pyrazol-5-yl)azepan-4-yl]carbamate A mixture of 5-chloro-1-methyl-4-nitro-1H-pyrazole (0.400 g, 2.48 mmol), tert-butyl azepan-4-yl carbamate (0.58 g, 2.7 mmol), EtOH (3 mL) and DIPEA (1.6 mL, 9.2 mmol) was irradiated in a microwave oven for 1 h at 130 C. The mixture was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel using CombiFlash apparatus, eluting with EtOAc/hexane (10-60%). The purification gave 0.580 g (69.0% yield) of the sub-title compound as a colorless oil. LCMS calc. for C11H18N5O4 (M+H-t-Bu+H)+: m/z=284.2. found: 284.1.

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, 5-Chloro-1-methyl-4-nitro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; INCYTE CORPORATION; Li, Yun-Long; Burns, David M.; Feng, Hao; Huang, Taisheng; Mei, Song; Pan, Jun; Vechorkin, Oleg; Ye, Hai-Fen; Zhu, Wenyu; Rafalski, Maria; Wang, Anlai; Xue, Chu-Biao; US2015/57265; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 42098-25-9, name is 5-Chloro-1-methyl-4-nitro-1H-pyrazole, molecular formula is C4H4ClN3O2, 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 5-Chloro-1-methyl-4-nitro-1H-pyrazole

Intermediate 43 RRN No.580,582N-(1-(4-Amino-1-methyl-1H-pyrazol-5-yl)-5-hydroxyazepan-4-yl)-2,2,2-trifluoroacetamide A solution of benzyl 4-hydroxy-5-(2,2,2-trifluoroacetamido)azepane-1-carboxylate (935 mg, 3.0 mmol) in MeOH (100 mL) was passed through the H-Cube (full H2, 50 C., flow rate: 1 mL/min, 30 mm 10% Pd/C cartridge). The solvent was removed under reduced pressure to give 4-hydroxy-5-(2,2,2-trifluoroacetamido)azepane as a pale yellow solid (514 mg). To a solution of this (500 mg, 2.21 mmol) in dry DMSO (10 mL) was added 5-chloro-1-methyl-4-nitro-1H-pyrazole from Example 1 (150 mg, 0.93 mmol) and potassium fluoride (513 mg, 8.85 mmol). The reaction mixture was heated at 65 C. for 16 hr. The mixture was poured into water (200 mL) and extracted with EtOAc (5×50 mL). The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. Purification of the residue by silica gel column chromatography (70% EtOAc/isohexane) gave 2,2,2-trifluoro-N-(5-hydroxy-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)azepan-4-yl)acetamide as a yellow solid (640 mg). A portion of this solid (200 mg, 0.57 mmol) was dissolved in MeOH (25 mL) and passed through the H-Cube (full H2, 50 C., flow rate: 1 mL/min, 30 mm 10% Pd/C cartridge). The solvent was removed under reduced pressure to give N-(1-(4-amino-1-methyl-1H-pyrazol-5-yl)-5-hydroxyazepan-4-yl)-2,2,2-trifluoroacetamide as an orange foam (172 mg, 68% over 3 steps). 1H NMR (400 MHz, DMSO) delta 9.22 (d, J=8.1 Hz, 1H), 6.83 (s, 1H), 4.84 (d, J=5.0 Hz, 1H), 3.91-3.73 (m, 2H), 3.32 (s, 3H), 3.28-2.96 (m, 4H), 2.00-1.75 (m, 4H). Exchangeable NH2 not observed.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 42098-25-9, its application will become more common.

Reference:
Patent; GENENTECH, INC.; Hodges, Alastair James; Matteucci, Mizio; Sharpe, Andrew; Sun, Minghua; Wang, Xiaojing; Tsui, Vickie H.; US2013/79321; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 42098-25-9, The chemical industry reduces the impact on the environment during synthesis 42098-25-9, name is 5-Chloro-1-methyl-4-nitro-1H-pyrazole, I believe this compound will play a more active role in future production and life.

Intermediate 2 5-(3A-Dihydro-2H-pyran-6-yl)-1-methyl-4-nitro-1H-pyrazole A mixture of 5-chloro-1-methyl-4-nitro-1H-pyrazole (200 mg, 1.25 mmol), potassium fluoride dihydrate (235 mg, 2.5 mmol) and 3,4-dihydro-2H-pyran-6-boronic acid pinacol ester (394 mg, 1.88 mmol) in THF (3 mL) was degassed by bubbling nitrogen through it for 15 min. Tris(dibenzylideneacetone)dipalladium/tri-tert-butyl phosphonium tetrafluoroborate mixture (mole ratio: 1/1.2, 151 mg, 0.13 mmol) was added and the mixture degassed for a further 10 min before being heated in the microwave at 85 C. for 2 hr. Water (10 mL) was added and the mixture extracted with EtOAc (3*5 mL). The combined organic layers were passed through a phase separation cartridge and concentrated under reduced pressure. Purification via silica gel chromatography (0-5% EtOAc/isohexane) gave 5-(3,4-dihydro-2H-pyran-6-yl)-1-methyl-4-nitro-1H-pyrazole as a yellow solid (215 mg, 82%). 1H NMR (400 MHz, CDCl3) delta 8.04 (s, 1H), 5.22 (t, J=3.9 Hz, 1H), 4.20 (t, J=5.1 Hz, 2H), 3.88 (s, 3H), 2.31-2.24 (m, 2H), 2.05-1.96 (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, 5-Chloro-1-methyl-4-nitro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Genentech, Inc.; Burch, Jason; Sun, Minghua; Wang, Xiaojing; Blackaby, Wesley; Hodges, Alastair James; Sharpe, Andrew; US2014/88117; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 42098-25-9, 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. 42098-25-9 name is 5-Chloro-1-methyl-4-nitro-1H-pyrazole, 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 78 tert-Butyl (1-(4-amino-1-methyl-1H-pyrazol-5-yl)piperidin-4-yl)methylcarbamate A solution of 5-chloro-1-methyl-4-nitro-1H-pyrazole from Example 1 (1.9 g, 11.77 mmol), 4-(boc-aminomethyl)piperidine (3.78 g, 17.66 mmol) and DIPEA (6.15 mL, 35.31 mmol) in EtOH (20 mL) was heated in a microwave at 130 C. for 1 hr. The solvent was removed under reduced pressure and the residue re-dissolved in DCM. The organic layer was washed with water, passed through a phase separation cartridge and concentrated under reduced pressure. The residue was purified via silica gel column chromatography (0-100% EtOAc/isohexane) to yield tert-butyl (1-(1-methyl-4-nitro-1H-pyrazol-5-yl)piperidin-4-yl)methylcarbamate as a yellow solid (3.95 g, 98%). To a solution of this solid (3.84 g, 11.30 mmol) in MeOH (125 mL) was added 10% Pd/C (0.42 g, 3.96 mmol) and ammonium formate (2.85 g, 45.2 mmol). The mixture was heated at 80 C. for 2.5 hr. The mixture was concentrated under reduced pressure and the residue was re-dissolved in EtOAc and washed with water. The organic layer was passed through a phase separation cartridge and concentrated under reduced pressure to give tert-butyl (1-(4-amino-1-methyl-1H-pyrazol-5-yl)piperidin-4-yl)methylcarbamate as a brown oil (3.49 g, 99%). 1H NMR (400 MHz, CDCl3) delta 7.04 (s, 1H), 4.63 (s, 1H), 3.64 (s, 3H), 3.11-3.07 (m, 6H), 2.67 (s, 2H), 1.77 (d, J=12.8 Hz, 2H), 1.45 (s, 9H), 1.39-1.26 (m, 2H). 1H hidden by water peak.

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

Reference:
Patent; GENENTECH, INC.; Hodges, Alastair James; Matteucci, Mizio; Sharpe, Andrew; Sun, Minghua; Wang, Xiaojing; Tsui, Vickie H.; US2013/79321; (2013); 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. 42098-25-9, name is 5-Chloro-1-methyl-4-nitro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 5-Chloro-1-methyl-4-nitro-1H-pyrazole

Example 64b 3-Fluoro-5-(4-methoxybenzyloxy)-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)azepane To a solution of tert-butyl 3-fluoro-5-(4-methoxybenzyloxy)azepane-1-carboxylate (740 mg, 0.21 mmol) in MeOH (5 mL) was added HCl (4 M in 1,4-dioxane, 5.3 mL, 21 mmol) and the solution was stirred at room temperature for 16 hr. The solvents were removed under reduced pressure and the residue was dissolved in MeOH and loaded onto an SCX column. The column was washed with MeOH and eluted with 7 N ammonia in MeOH. The solvents were removed under reduced pressure to afford a yellow oil. To a solution of this oil in dry DMSO (15 mL) was added potassium fluoride (0.32 g, 8.4 mmol) and 5-chloro-1-methyl-4-nitro-1H-pyrazole (372 mg, 2.31 mmol) and the mixture was heated at 65 C. for 16 hr. After cooling to room temperature, the mixture was diluted with water (300 mL) and extracted with EtOAc (2*50 mL). The combined organic layers were washed with water (3*50 mL) and the solvent was removed under reduced pressure. Purification via silica gel column chromatography (20-100% EtOAc/isohexane) gave 3-fluoro-5-(4-methoxybenzyloxy)-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)azepane as a yellow oil (300 g, 55% over two steps). 1H NMR (400 MHz, CDCl3) delta 7.33-7.23 (m, 3H), 6.89-6.86 (m, 2H), 4.82-4.66 (m, 2H), 4.49-3.93 (m, 1H), 3.81 (s, 3H), 3.30-2.99 (m, 4H), 2.95-2.74 (m, 4H), 2.35-2.03 (m, 2H), 1.98-1.83 (m, 2H).

The synthetic route of 42098-25-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; Hodges, Alastair James; Matteucci, Mizio; Sharpe, Andrew; Sun, Minghua; Wang, Xiaojing; Tsui, Vickie H.; US2013/79321; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 42098-25-9, These common heterocyclic compound, 42098-25-9, name is 5-Chloro-1-methyl-4-nitro-1H-pyrazole, 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.

tert-Butyl 8-(1-methyl-4-nitro-1H-pyrazol-5-yl)-2,8-diazaspiro[4.5]decane-2-carboxylate A mixture of 5-chloro-1-methyl-4-nitro-1H-pyrazole from Example 1 (150 mg, 0.93 mmol), tert-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (244 mg, 1.02 mmol) and DIPEA (1 mL) in EtOH (3 mL) was heated at 130 C. in a microwave for 2 hr. The solvent was removed under reduced pressure and the crude product was purified via silica gel column chromatography (50% EtOAc/isohexane) to give tert-butyl 8-(1-methyl-4-nitro-1H-pyrazol-5-yl)-2,8-diazaspiro[4.5]decane-2-carboxylate as a yellow oil (245 mg, 72%). 1H NMR (400 MHz, CDCl3) delta 8.02 (s, 1H), 3.76 (s, 3H), 3.49-3.39 (m, 2H), 3.30-3.00 (m, 6H), 1.90-1.60 (m, 6H), 1.55 (s, 9H).

Statistics shows that 5-Chloro-1-methyl-4-nitro-1H-pyrazole is playing an increasingly important role. we look forward to future research findings about 42098-25-9.

Reference:
Patent; GENENTECH, INC.; Hodges, Alastair James; Matteucci, Mizio; Sharpe, Andrew; Sun, Minghua; Wang, Xiaojing; Tsui, Vickie H.; US2013/79321; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 42098-25-9, name is 5-Chloro-1-methyl-4-nitro-1H-pyrazole, 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. COA of Formula: C4H4ClN3O2

KO’Bu (938 mg, 8.36 mmol) was added to a stirred solution of 5-chloro-l-methyl-4- nitro-lH-pyrazole (900 mg, 5.57 mmol) and cyclopropanol (970.713 mg, 16.713 mmol) in MeCN (7.27 mL) at rt. Addition was done portionwise. The mixture was stirred at rt for 3hours. Water was added and the mixture acidified with 3N HCl(aq). The reaction mixture was extracted with DCM, dried over MgS04, filtered and evaporated. A purification was performed via preparative LC (Stationary phase: irregular SiOH 15- 40muiotaeta 80g GraceResolv, Mobile phase: gradient from 100% DCM to 98% DCM, 2% MeOH, 0, 1% NH4OH) to afford intermediate 620 (470 mg, yield 46 %).

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier, Alexis, Georges; LIGNY, Yannick, Aime, Eddy; GROSS, Gerhard, Max; JACOBY, Edgar; MEERPOEL, Lieven; GREEN, Simon, Richard; HYND, George; KULAGOWSKI, Janusz, Jozef; MACLEOD, Calum; MANN, Samuel, Edward; (472 pag.)WO2018/2217; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 42098-25-9, 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. 42098-25-9, name is 5-Chloro-1-methyl-4-nitro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step C. tert-Butyl [1-(1-methyl-4-nitro-1H-pyrazol-5-yl)azepan-4-yl]carbamate A mixture of 5-chloro-1-methyl-4-nitro-1H-pyrazole (0.400 g, 2.48 mmol), tert-butyl azepan-4-yl carbamate (0.58 g, 2.7 mmol), EtOH (3 mL) and DIPEA (1.6 mL, 9.2 mmol) was irradiated in a microwave oven for 1 h at 130 C. The mixture was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel using CombiFlash apparatus, eluting with EtOAc/hexane (10-60%). The purification gave 0.580 g (69.0% yield) of the sub-title compound as a colorless oil. LCMS calc. for C11H18N5O4 (M+H-t-Bu+H)+: m/z=284.2. found: 284.1.

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, 5-Chloro-1-methyl-4-nitro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; INCYTE CORPORATION; Li, Yun-Long; Burns, David M.; Feng, Hao; Huang, Taisheng; Mei, Song; Pan, Jun; Vechorkin, Oleg; Ye, Hai-Fen; Zhu, Wenyu; Rafalski, Maria; Wang, Anlai; Xue, Chu-Biao; US2015/57265; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 42098-25-9, name is 5-Chloro-1-methyl-4-nitro-1H-pyrazole, 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 42098-25-9, Computed Properties of C4H4ClN3O2

a mixture of (Z)-2,3,6,7-tetrahydro-1H-azepine hydrochloride (32.3 g; 0.24 mol), 5-chloro-1-methyl-4-nitro-1H-pyrazole (37.2 g; 0.23 mol), potassium fluoride (56.24 g; 0.96 mol), and diisopropylethylamine (64 ml; 0.362 mol) in anhydrous DMSO (650 ml) was heated at 75 C for 21 h. On cooling, the mixture was poured into water (1,500 ml), extracted with ethyl acetate (4 × 500 ml), and the combined organics washed with water (2 × 400 ml) and brine (300 ml) then dried (MgSO4). The solvent was removed under reduced pressure to afford (Z)-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)-2,3,6,7-tetrahydro-1H-azepine as a light brown solid (50.74 g; 99%). 1H-NMR (400 MHz, CDCl3) delta 8.00 (s, 1H), 5.95-5.85 (m, 2H), 3.80(s, 3H), 3.30-3.20 (m, 4H), 2.45-2.35 (m, 4H). LC-MS (ESI m/z): 223.1 [M + H+].

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, 5-Chloro-1-methyl-4-nitro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.