Category: 28466-26-4

Electric Literature of 28466-26-4, These common heterocyclic compound, 28466-26-4, name is 4-Aminopyrazole, 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.

As shown in step 5-i of Scheme 5, methyl 4-bromo-2-(bromomethyl)benzoate (Compound 2018, 2.08 g, 6.75 mmol; prepared by reacting l-(4-bromo-2- methylphenyl)ethanone with NBS),lH-pyrazol-4-amine (561 mg, 6.75 mmol), and DIEA (873 mg, 1.18 mL, 6.75 mmol) were combined in DMF (7.78 mL) and heated at 110 C for 90 min. The reaction mixture was diluted with MeOH (60 mL) and the resulting white crystaline solid was collected by filtration and dried under vacuum to give 5-bromo-2-(lH- pyrazol-4-yl)isoindolin-l-one (Compound 2019, 1.21 g, 4.35 mmol, 64% yield): ESMS (Mu+Eta) 279.99

Statistics shows that 4-Aminopyrazole is playing an increasingly important role. we look forward to future research findings about 28466-26-4.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; ARONOV, Alex; COME, Jon, H.; DAVIES, Robert, J.; PIERCE, Albert, C.; WANG, Jian; NANTHAKUMAR, Suganthini; CAO, Jingrong; BANDARAGE, Upul, K.; KRUEGER, Elaine; TIRAN, Amaud, Le; LIAO, Yusheng; MESSERSMITH, David; COLLIER, Philip, N.; GREY, Ronald; O’DOWD, Hardwin; HENDERSON, James, A.; GRILLOT, Anne-Laure; WO2011/87776; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 28466-26-4, 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. 28466-26-4 name is 4-Aminopyrazole, 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.

[00606] Synthesis of compound 1-78. Compound 1-78 was prepared from compounds 3.4 and 96.2 using protocol described in Example 94. . LCMS (ES, m/z): 440 [M+H]+; 1H-NMR (300 MHz, DMSO) delta 8.87 (1H, s), 7.82 (1H, brs), 7.52 (1H, brs), 5.71 (1H, d), 4.05-3.89 (1H, m), 3.58 (4H, brs), 3.01-2.95 (2H, m), 2.84-2.79 (2H, m), 2.50 (4H, m), 2.42-2.34 (2H, m), 2.26- 2.18 (1H, m), 2.05 (2H, d), 1.92 (2H, d), 1.47-1.30 (4H, m). [00599] Example 94. Synthesis of 2-(4-((4-(((lr,4r)-4-morpholinocyclohexyl)amino)-6,7- dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-2-yl)amino)-lH-pyrazol-l-yl)acetate, Example 1-76 [00600] To a solution of intermediate 3.4 (50 mg, 0.13 mmol, 1.00 equiv) and 2-(4-amino- lH-pyrazol-l-yl)acetic acid (36 mg, 0.26 mmol, 2.00 equiv) in isopropanol (5 mL) was added hydrochloric acid (4 M in dioxane, 0.1 mL) at room temperature. The reaction was stirred for 2 h at 140 C and irradiated in microwave. The resulting mixture was concentrated under vacuum and resulting crude was purified to yield compound 1-76 as a yellow solid. LCMS (ES, m/z) 540 [M+H]+. 1H NMR (300 MHz, d6-OMSO, ppm): delta 8.99 (s, 1H), 7.90 (s, 1H), 7.51 (s, 1H), 7.26-7.06 (m, 1H), 5.79-5.71 (m, 1H), 4.99-4.91 (m, 3H), 4.01-3.99 (m, 1H), 3.77-51 (m, 4H), 3.05-2.98 (m, 2H), 2.83-2.73 (m, 2H), 2.61-2.53 (m, 5H), 2.40-2.35 (m, 2H), 2.01-1.94 (m, 2H), 1.49-1.35 (m, 4H), 1.20-1.15 (m, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Aminopyrazole, and friends who are interested can also refer to it.

Reference:
Patent; NIMBUS IRIS, INC.; CHAUDHARY, Divya; KAPELLER-LIBERMANN, Rosana; WO2014/194242; (2014); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 28466-26-4, name is 4-Aminopyrazole, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 4-Aminopyrazole

Intermediate 25: 1 ,1-Dimethylethyl 6-[(1 /-/-pyrazol-4-ylamino)carbonyl1-3,4-dihydro- 2(1 HVisoalphauinolinecarboxylate; To a solution of 1 H-pyrazol-4-amine (1.87 g, 22.5 mmol), N-(3-dimethylaminopropyl)- N’-ethylcarbodiimide hydrochloride (5.18 g, 27 mmol), 1-hydroxybenzotriazole hydrate (3.65 g, 27 mmol) and triethylamine (6.3 ml_, 45 mmol) in DMF was added 2- {[(I J-dimethylethyOoxylcarbonylJ-i ^^^-tetrahydro-theta-isoquinolinecarboxylic acid (5.62 g, 20.3 mmol) and the reaction mixture was stirred at room temperature for 16 hours. The volatiles were removed under reduced pressure, the residue was dissolved in MeOH and potassium hydroxide (5.04 g, 90 mmol), water (100 ml.) was added and the mixture was heated at 500C for 15 min. The MeOH was evaporated under reduced pressure and the solid which crystallized was filtered and recrystallized from acetonitrile to give the title compound as a solid (3.7 g, 48%). LC/MS: m/z 341 (M-H)+, Rt: 2.80 min.

According to the analysis of related databases, 28466-26-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/74824; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 28466-26-4, name is 4-Aminopyrazole, 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: C3H5N3

Neat 1 H-pyrazol-4-amine (55.2 mg, 0.66 mmol) was added in one charge to a stirred solution of 5-bromo-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 5, method D; 170 mg, 0.55 mmol), EDC (318 mg, 1.66 mmol) and HOBT (254 mg, 1.66 mmol) in N,N-dimethylformamide (4 ml) in air at room temperature. The reaction mixture was stirred at room temperature overnight. Water (30 ml) was added, and the mixture was extracted with ethyl acetate (50 ml x 2). The organic layers were combined, dried over MgSO,,, and concentrated in vacuo. The residue was washed with ethyl acetate yield the title compound as a brown solid. 180 mg.1HNMR (400 MHz, DMSO-c/6): 5.26 (s, 2H), 7.24 (d, 1 H), 7.35-7.45 (m, 4H), 7.52 (d, 2H), 7.65-7.68 (m, 1 H), 7.77 (d, 1 H), 7.93 (s, 1 H), 10.21 (s, 1 H), 12.66 (s, 1 H).MS (electrospray): m/z [M+H]+ = 372

The synthetic route of 4-Aminopyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; NICHOLS, Paula Louise; EATHERTON, Andrew John; BAMBOROUGH, Paul; JANDU, Karamjit Singh; PHILPS, Oliver James; ANDREOTTI, Daniele; WO2011/38572; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 28466-26-4, A common heterocyclic compound, 28466-26-4, name is 4-Aminopyrazole, molecular formula is C3H5N3, 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.

Neat 1 H-pyrazol-4-amine (49.0 mg, 0.59 mmol) was added in one charge to a stirred solution of 2-[(phenylmethyl)oxy]-5-(4-pyndinyl)benzoic acid (may be prepared as described in Description 79; 150 mg, 0.49 mmol), EDC (283 mg, 1.47 mmol) and HOBT (226 mg, 1.47 mmol) in dimethylformamide (4 ml) in air at room temperature. The reaction mixture was stirred at room temperature overnight. 30 ml water was added, and the mixture was extracted with ethyl acetate (70 ml x 2). The organic layers were combined, dried over MgS04l and concentrated in vacuo. The residue was further purified by pre-HPLC (Gilson GX-281 ; Shimadzu 15mueta? 250*20mm; A: l OmMolNH4HC03/Water; B: CH3CN) to yield the title compound as a white solid. 50 mg.1HNMR (400 MHz, DMSO-cfe): 5.34 (s, 2H), 7.34-7.44 (m, 4H), 7.55 (d, 2H), 7.74 (d, 4H), 7.95-7.98 (m, 1 H), 8.09 (d, 1 H), 8.62 (d, 2H), 10.25 (s, 1 H), 12.65 (s, 1 H).MS (electrospray): m/z [M+H]+ = 371

The synthetic route of 28466-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; NICHOLS, Paula Louise; EATHERTON, Andrew John; BAMBOROUGH, Paul; JANDU, Karamjit Singh; PHILPS, Oliver James; ANDREOTTI, Daniele; WO2011/38572; (2011); 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. 28466-26-4, name is 4-Aminopyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C3H5N3

Imine (I1) A solution of 4-aminopyrazole (10) (10.5 g, 126 mmol), ethylacetoacetate (18.0 g, 140 mmol, 1.05 eq.) and a catalytic amount of para-toluenesulfonic acid monohydrate (1.3 g, 6.65 mmol, 5%) in 100 mL of benzene was refluxed with a Dean-Stark trap for about 1 hour. The end of reaction checked by TLC (Ethylacetate/Hexane 1/1, 4-aminopyrazole Rf=0.1, imine Rf=0.5, UV active, brown after overnight). Solvents were removed under vacuum and the imine was purified by running through a short silica chromatography column to give the desired product (11) as a tan solid (22.4 g, 125 mmol, 91%). GC/MS: m/z=195 (100%).

The synthetic route of 28466-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Neurocrine Biosciences, Inc.; US6531475; (2003); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 28466-26-4, 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 28466-26-4 as follows.

To a solution of 1H-pyrazol-4-amine (300 mg, 95% purity, 3.43 mmol) in acetonitrile(17 mL) were added 2,2-difluoroethyl trifluoromethanesulfonate (690 p1, 5.1 mmol, CASRN 74427-22-8), powdered potassium carbonate (1 .06 g, 7.65 mmol), and triethylamine (720 pL, 5.1 mmol). The mixture was heated to 12000 overnight. For work-up, it was filtered, and the solid was rinsed with ethyl acetate. Concentraction of the filtrate in vacuo followed by flash chromatography led to the title compound (505 mg, 90% yield, 90%purity).LC-MS (Method B): Rt = 0.43 mm MS (ESIpos): mlz = 148 (M–H)1HNMR (400MHz, DMSO-d6) oe [ppm]: 3.23 (tdd, 2H), 4.72 (t, 1H), 6.05 (tt, 1H), 7.12 (s,2H), 12.10 (s, 1H).

According to the analysis of related databases, 28466-26-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; WERNER, Stefan; MESCH, Stefanie; CLEVE, Arwed; BRAeUER, Nico; HERBERT, Simon, Anthony; KOCH, Markus; DAHLLOeF, Henrik; OSMERS, Maren; HARDAKER, Elizabeth; LISHCHYNSKYI, Anton; (673 pag.)WO2017/191000; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 28466-26-4, The chemical industry reduces the impact on the environment during synthesis 28466-26-4, name is 4-Aminopyrazole, I believe this compound will play a more active role in future production and life.

To a solution of 1 H-pyrazol-4-amine (1 g, 95% purity, 11 .4 mmol) in acetonitrile (57 mL) were added (bromomethyl)cyclopropane (1.65 ml, 17.1 mmol, GAS-RN 7051-34-5),powdered potassium carbonate (3.95 g, 28.6 mmol), and triethylamine (2.39 mL,17.1 mmol). The mixture was heated to 900 for 4h and stirred at room temperatureovernight. For work-up, it was filtered, and the solid was rinsed with ethyl acetate.Goncentration of the filtrate in vacuo followed by flash chromatography led to N(cyclopropylmethyl)-1 H-pyrazol-4-amine (416 mg, 24% yield, 90% purity).LG-MS (Method B): Rt = 0.54 mm; MS (ESIpos): m/z = 138 (M÷H)1HNMR (400MHz, DMSO-d6) oe [ppm]: 0.16 (m, 2H), 0.42 (m, 2H), 0.99 (m, 1H), 2.68 (m,2H), 4.23 (m, 1H), 7.03 (5, 2H), 12.01 (5, 1H).As additional fraction, N, N-bis(cyclopropylmethyl)- 1 H-pyrazol-4-am me was isolated(657 mg, 27% yield, 90% purity).LG-MS (Method B): Rt = 0.97 mm; MS (ESIpos): m/z = 192 (M÷H)1HNMR (400MHz, DMSO-d6) oe [ppm]: 0.06 (m, 4H), 0.33 (m, 4H), 0.84 (m, 2H), 2.82 (d,4H), 7.07 (5, 2H), 12.07 (5, 1H).

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, 4-Aminopyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; WERNER, Stefan; CLEVE, Arwed; (139 pag.)WO2018/210729; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 28466-26-4, The chemical industry reduces the impact on the environment during synthesis 28466-26-4, name is 4-Aminopyrazole, I believe this compound will play a more active role in future production and life.

To a solution of 1 H-pyrazol-4-amine (1 g, 95% purity, 11 .4 mmol) in acetonitrile (57 mL) were added (bromomethyl)cyclopropane (1.65 ml, 17.1 mmol, GAS-RN 7051-34-5),powdered potassium carbonate (3.95 g, 28.6 mmol), and triethylamine (2.39 mL,17.1 mmol). The mixture was heated to 900 for 4h and stirred at room temperatureovernight. For work-up, it was filtered, and the solid was rinsed with ethyl acetate.Goncentration of the filtrate in vacuo followed by flash chromatography led to N(cyclopropylmethyl)-1 H-pyrazol-4-amine (416 mg, 24% yield, 90% purity).LG-MS (Method B): Rt = 0.54 mm; MS (ESIpos): m/z = 138 (M÷H)1HNMR (400MHz, DMSO-d6) oe [ppm]: 0.16 (m, 2H), 0.42 (m, 2H), 0.99 (m, 1H), 2.68 (m,2H), 4.23 (m, 1H), 7.03 (5, 2H), 12.01 (5, 1H).As additional fraction, N, N-bis(cyclopropylmethyl)- 1 H-pyrazol-4-am me was isolated(657 mg, 27% yield, 90% purity).LG-MS (Method B): Rt = 0.97 mm; MS (ESIpos): m/z = 192 (M÷H)1HNMR (400MHz, DMSO-d6) oe [ppm]: 0.06 (m, 4H), 0.33 (m, 4H), 0.84 (m, 2H), 2.82 (d,4H), 7.07 (5, 2H), 12.07 (5, 1H).

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, 4-Aminopyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; WERNER, Stefan; CLEVE, Arwed; (139 pag.)WO2018/210729; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 28466-26-4,Some common heterocyclic compound, 28466-26-4, name is 4-Aminopyrazole, molecular formula is C3H5N3, 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 library of compounds in which R4 was various groups having the formula [CONHR »] was prepared by the process described above using 4-fluoro-3-nitrobenzoic acid, as follows: [72] Aldehyde resin was mixed with a primary amine (R17-NH2) in [DICHLOROETHANE] (DCE), triethylorthoformate (TEOF), and DMF (containing [1%] acetic acid) in a 1: 1: 1 ratio. After shaken overnight, sodium triacetoxyborohydride (20 eq. ) dissolved in DMF was added (Abdel-Magid, A. F. , et al., Tetrahedron Lett, 3 1: 5595-5598 (1990) ). After the mixture was shaken at room temperature overnight, the resin was filtered and washed with DMF (3 x 5 mL), [MEOH] [(3 X 5] mL), DMF [(3 X 5] mL), [MEOH] [(3 X 5] mL), and [CH2CL2] [(3 X 5] mL). The resin was washed twice with 5 mL DMF containing [1%] Hunig’s base. To the filtered resin was added a mixture of 4-fluoro-3-nitrobenzoic acid (FNBA, 10 eq. ) and diisopropylcarbodiimide (DIC, 5 eq. ) in 2: 1 DMF : DCM. After shaking at room temperature overnight, the resin was filtered and washed with DMF (3 x 5 mL) and [CH2C12] (3 x 5 mL). [73] The resin was shaken with a primary amine [(R2-NH2)] in DMF for 8 hrs, filtered, and washed with DMF (6 x 5 mL), [MEOH] [(3 X 5] mL), and CH2C12 (3 x 5 mL). The aryl nitro group was reduced by the addition of tin (II) chloride dihydrate (20 eq. , >2 M) and N-methyl morpholine (NMM, 20 eq. ) in N-methyl pyrrolidinone (NMP). After shaken at room temperature overnight, the resin was filtered and washed with NMP (3 x 5 mL), [MEOH] (3 x 5 mL), and [CH2CI2 (3 X 5] mL). The resulting resin was shaken at room temperature with cyanogen bromide (5 eq. ) overnight, filtered, and washed with CH2Cl2 (3 x 5 mL), [MEOH] (3 x 5 mL), and CH2CI2 (3 x 5 mL). To produce a free amine, the resin was shaken for 30 min. in CHCl2 with the addition of sodium methoxide in methanol, filtered, and washed with CH2Cl2 [(4 X 5] mL). [[74]] In the final diversification step, the resin was heated at 500 C in DMF with a mono- substituted epoxide [[RLCH (-CH2O-)].] After shaking for 2 to 4 days the resin was filtered and washed with DMF (5 x 5 mL), [MEOH] [(3 X 5] mL), and CH2Cl2 (3 x 5 mL). T he resin-bound benzimidazole was cleaved from the solid-support by treatment with TFA: [CH2C12] (2: 3) for 1 hour at room temperature.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Aminopyrazole, its application will become more common.

Reference:
Patent; Taktix Corporation; WO2003/105779; (2003); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics