Tag: M.W:100-200

82560-12-1,Some common heterocyclic compound, 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, molecular formula is C7H13N3, 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.

A5. General Method for the Synthesis of BOC-Protected Pyrazoles; 5-Amino-3-tert-butyl-N1-(tert-butoxycarbonyl)pyrazole; To a solution of 5-amino-3-tert-butylpyrazole (3.93 g, 28.2 mmol) in CH2Cl2 (140 mL) was added di-tert-butyl dicarbonate (6.22 g, 28.5 mmol) in one portion. The resulting solution was stirred at room temp. for 13 h, then diluted with EtOAc (500 mL). The organic layer was washed with water (2¡Á300 mL), dried (MgSO4) and concentrated under reduced pressure. The solid residue was triturated (100 mL hexane) to give the desired carbamate (6.26 g, 92%); mp 63-64 C.; TLC Rf (5% acetone/95% CH2Cl2); 1H-NMR (DMSO-d6) delta 1.15 (s, 9H), 1.54 (s, 9H), 5.22 (s, 1H), 6.11 (s, 2H); FAB-MS m/z ((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 3-Amino-5-tert-butylpyrazole, its application will become more common.

1125-29-7, 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. 1125-29-7 name is 1,3,5-Trimethyl-1H-pyrazole-4-carboxylic acid, 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 102 1,3,5-Trimethyl-1H-pyrazole-4-carboxylic acid {4-[3-cyclopropylmethyl-1-(2-fluorobenzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-methyl-amide A mixture of 1,3,5-trimethyl-1H-pyrazole-4-carboxylic acid (71 mg, 0.46 mmol) in dichloromethane (2.5 mL) at 0 C. was treated with triphenylphosphine (145 mg, 0.55 mmol) and N-chlorosuccinimide (74 mg, 0.55 mmol). This mixture was stirred at 0 C. for 30 min and then was warmed to 25 C. for 10 min. At this time, the reaction was treated with a solution of 3-cyclopropylmethyl-1-(2-fluoro-benzyl)-8-(4-methylamino-benzyl)-3,7-dihydro-purine-2,6-dione (400 mg, 0.92 mmol) in dichloromethane (2.5 mL). The reaction was stirred at 25 C. for 24 h. At this time, the reaction was diluted with dichloromethane (50 mL) and then was washed with a saturated aqueous sodium bicarbonate solution (1*50 mL). The aqueous layer was re-extracted with dichloromethane (2*50 mL). The combined organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 3:97 methanol/dichloromethane) afforded impure product. The resulting residue was purified by HPLC (15-60% acetonitrile/water (0.075% trifluoroacetic acid in both solvents) over 40 min). Fractions with the desired product were combined and concentrated in vacuo. The resulting residue was diluted with dichloromethane (50 mL) and was washed with a saturated aqueous sodium bicarbonate solution (50 mL). The water layer was re-extracted with dichloromethane (2*50 mL). The organic layers were combined and dried with magnesium sulfate, filtered and concentrated under reduced pressure. The resulting solid was dried in vacuo for 24 h to afford 1,3,5-trimethyl-1H-pyrazole-4-carboxylic acid {4-[3-cyclopropylmethyl-1-(2-fluoro-benzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-methyl-amide (169 mg, 65%) as a white solid: (ES)+-HRMS m/e calcd for C31H32N7O3F (M+H)+ 570.2623, found 570.2619.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3,5-Trimethyl-1H-pyrazole-4-carboxylic acid, and friends who are interested can also refer to it.

20154-03-4, 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 20154-03-4 as follows.

Example 104: Preparation of (S)-3-methyl-2-(8-(3-(trifluoromethyl)-lH- pyrazol-l-yl)dibenzo[b,d]furan-3-sulfonamido)butanoic acidStep 1 : Preparation of (SWert-butyl 3-methyl-2-(8-(3-(trifluoromethvO-lH-pyrazol- l-yDdibenzo[b,d1furan-3-ylsulfonamido)butanoate[0234] (S)-Tert-butyl 2-(8-bromodibenzo[b,d]furan-3-sulfonamido)-3- methylbutanoate from (Example 103, Step 2, 485 mg, 1 mmol), 3- (trifluoromethyl)pyrazole (274 mg, 2 mmol), /roem’-N,N’-dimethyl-l,2- cyclohexanediamine (29 mg, 0.2 mmol), copper (I) iodide (CuI, 10 mg, 0.05 mmol), and K3PO4 (450 mg, 21 mmol) were mixed in 2 mL of toluene. The mixture was irradiated with microwave at 13O0C for 3 hours. The reaction mixture was purified by a preparative etaPLC to give 313 mg of (S)-/erf-butyl 3-methyl-2-(8-(3- (trifluoromethyl)-l/7-pyrazol-l-yl)dibenzo[b,d]furan-3-ylsulfonamido)butanoate as a white solid in 58percent yield.

According to the analysis of related databases, 3-(Trifluoromethyl)-1H-pyrazole, the application of this compound in the production field has become more and more popular.

113100-53-1, 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. 113100-53-1 name is 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid, 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.

1-Methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid N’-[trans-4-(6-methoxy-3-methyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-cyclohexanecarbonyl]-hydrazide Trans-N’-4-(6-Methoxy-3-methyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-cyclohexanecarboxylic acid hydrazide (180 mg, 0.49 mmol), HATU (223 mg, 0.59 mmol), TEA (0.15 mL, 1.08 mmol) and 3-(trifluoromethyl)-1H-pyrazol-4-carboxylic acid (114 mg, 0.59 mmol) were dissolved in DMF (2 mL) and the mixture was left stirring overnight at r.t. The solvent was removed in vacuo and the crude was washed with MeOH to give the titled compound (75 mg, yield 33%). 1HNMR (DMSO) delta: 1.00-1.10 (2H, m), 1.27-1.37 (2H, m), 1.63-1.66 (2H, m), 1.73-1.76 (3H, m), 2.13-2.20 (1H, m), 3.27 (3H, s), 3.64 (2H, d, J=8.0 Hz), 3.74 (3H, s), 3.95 (3H, s), 6.62 (1H, dd, J=8.0 and 1.6 Hz), 6.85 (1H, d, J=1.6 Hz), 7.01 (1H, d, J=8.0 Hz) 8.32 (1H, s), 9.77 (1H, bs), 10.06 (1H, bs). C22H25F3N6O4 Mass (calculated) [508.50]. found [M+H+]=509, RT=1.17 (method f)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid, and friends who are interested can also refer to it.

16034-46-1, 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 16034-46-1 as follows.

To a solution of tert-butyl [2-(2,4-dichlorobenzyl)-4-methyl-1,3-thiazol-5-yl]carbamate (536 mg, 1.44 mmol) obtained in Example 155-D) in ethanol (0.9 mL) was added dropwise concentrated hydrochloric acid (3 mL) at 0C, and the mixture was stirred at room temperature for 15 min. The reaction mixture was cooled to 0C, neutralized with 8M aqueous sodium hydroxide solution (4.5 mL), adjusted to pH 10-11 with saturated aqueous sodium hydrogen carbonate solution, and extracted twice with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was dissolved in DMA (5 mL), and 1-methyl-1H-pyrazole-5-carboxylic acid (218 mg, 1.73 mmol) obtained in Example 1-A), HATU (658 mg, 1.73 mmol) and DIEA (0.126 mL, 0.72 mmol) were added at 0C. The reaction mixture was stirred at 60C for 3 hr, water was added, and the mixture was extracted twice with ethyl acetate. The organic layer was washed successively with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: hexane-ethyl acetate (9:1-0:1)] and basic silica gel column chromatography [eluent: hexane-ethyl acetate (9:1-0:1)], and crystallized from ethyl acetate-hexane to give the title compound (314 mg) as yellow crystals (yield 57%). MS (ESI+): [M+H]+ 381. 1H NMR (300 MHz, CDCl3) delta 2.39 (3H, s), 4.20 (3H, s), 4.34 (2H, s), 6.67 (1H, d, J = 1.9 Hz), 7.15-7.36 (2H, m), 7.42 (1H, d, J = 2.3 Hz), 7.52 (1H, d, J = 1.9 Hz), 7.70 (1H brs).

According to the analysis of related databases, 1-Methyl-1H-pyrazole-5-carboxylic acid, the application of this compound in the production field has become more and more popular.

4522-35-4, Adding some certain compound to certain chemical reactions, such as: 4522-35-4, name is 3-Iodo-1H-pyrazole, 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 4522-35-4.

1-(chloromethyl)-4-methoxy-benzene (2.10 mL, 15.5 mmol) was added to a stirred mixture of 3-iodo-1H-pyrazole (2.01 g, 10.4 mmol) and Cs2CO3 (6.70 g, 20.6 mmol) in DMF (30.0 mL). The reaction mixture was stirred at 60 C for 2 hours and then, cooled to room temperature. Water (100mL) was added and aqueous was extracted with EtOAc (3 x 50 mL). Combined organic extracts were washed with aqueous saturated NH4Cl (25 mL) solution, brine (25 mL) and dried over MgSO4. The mixture was filtered and concentrated to afford 4.06 g of crude material. The residue was adsorbed on silica using DCM and purified by silica gel chromatography to afford 3-iodo-1-[(4- methoxyphenyl)methyl]pyrazole and 5-iodo-1-[(4-methoxyphenyl)methyl]pyrazole (3.18 g, 98%) as a white solid as a ca.5:1 mixture of regioisomers. Major Regioisomer: 1H NMR (400 MHz, CDCl3) 7.23 – 7.15 (m, 3H), 7.12 (d, J = 2.3 Hz, 1H), 6.92 – 6.85 (m, 2H), 6.40 (d, J = 2.3 Hz, 1H), 5.24 (s, 2H). : ESI-MS m/z calc.313.9916, found 314.98 (M+1)+; Retention time: 0.93 minutes Using Method J A mixture of tert-butyl 2,2-dimethyl-3-oxo-piperazine-1-carboxylate (915 mg, 4.01 mmol), regioisomers mix of 5-iodo-1-[(4-methoxyphenyl)methyl]pyrazole/3- iodo-1-[(4-methoxyphenyl)methyl]pyrazole (1.51 g, 4.81 mmol), iodocopper (381.7 mg, 2.00 mmol), N,N’-dimethylethane-1,2-diamine (353.3 mg, 426.7 muL, 4.01 mmol) and K3PO4 (1.702 g, 8.02 mmol) in DMF (18.3 mL) was heated at 120 C for 3.5 hours. The reaction mixture was cooled to r.t. and filtered to remove the copper salts. The filtrate was diluted with water and aqueous was extracted twice with ethyl acetate. Organic extracts were washed with water, followed with brine, dried over Na2SO4, filtered and (0666) concentrated under reduced pressure. The recovered crude compound was purified by silica gel chromatography to give a mixture of the tert-butyl 4-[2-[(4- methoxyphenyl)methyl]pyrazol-3-yl]-2,2-dimethyl-3-oxo-piperazine-1-carboxylate and the tert-butyl 4-[1-[(4-methoxyphenyl)methyl]pyrazol-3-yl]-2,2-dimethyl-3-oxo- piperazine-1-carboxylate (1.603 g, 96%). Major regioisomer: 1H NMR (400 MHz, DMSO-d6) 7.70 (d, J = 2.3 Hz, 1H), 7.22 – 7.11 (m, 2H), 6.91 – 6.81 (m, 2H), 6.61 (d, J = 2.3 Hz, 1H), 5.14 (s, 2H), 3.86 – 3.79 (m, 2H), 3.69 (s, 3H), 3.66 – 3.58 (m, 2H), 1.58 (s, 6H), 1.40 (s, 9H). ESI-MS m/z calc.414.2267, found 416.38 (M+1)+

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 4522-35-4.

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 20154-03-4 as follows. 20154-03-4

EXAMPLE 7 (5,11-Dihydro-pyrido[2,3-b][1,5]benzodiazepin-6-yl)-[2-trifluoromethyl-4-(3-trifluoromethyl-pyrazol-1-yl)-phenyl]-methanone Sodium hydride (60percent suspension in oil, 0.17 g, 4.25 mmol) was washed with hexane, dried under nitrogen and resuspended in dry dimethylformamide (10 mL). 3-trifluoromethyl pyrazole (0.34 g, 2.5 mmol) was added in one portion. After the gas evolution subsided stirring was continued at room temperature. The (5,11-dihydro-pyrido [2,3-b][1,5]benzodiazepin-6-yl)- (4-fluoro-2-trifluoromethyl-phenyl)methanone of Example 4, Step B (0.75 g, 1.94 mmol) was added in one portion and the mixture was placed in an oil bath (preheated at 130¡ã C.) overnight. After cooling, the mixture was partitioned between water and ethyl acetate. The organic extracts were dried over sodium sulfate, and evaporated to dryness in vacuo. The residue was crystallized from ethanol to yield the title compound (0.57 g, 57.3percent) as an off-white solid, m.p. 127-129¡ã C. NMR (DMSO-d6, 400 MHz): delta 4.19 and 5.46 (dd, 2H, CONCH2), 6.54 (m, 1H), 6.70 (m, 1H), 6.80 (m, 1H), 7.02 (m, 1H), 7.07 (m, 1H, pyrazole CH), 7.29 (m, 1H), 7.61 (m, 1H), 8.00 (m, 1H), 8.05-8.16 (m, 2H), 8.84 (m, 1H, pyrazole CH), 9.63 (s, 1H, NH) MS (EI, m/z): 503 [M]+ Anal. Calc’d for C24 H15 F6 N5 O: C 57.26, H 3.00, N 13.91. Found: C 57.07, H 2.97, N 13.58

According to the analysis of related databases, 20154-03-4, the application of this compound in the production field has become more and more popular.

2075-46-9, These common heterocyclic compound, 2075-46-9, name is 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.

Example 16 Preparation of 5-bromo-1H-pyrazol-4-amine, HBr A mixture of 4-nitro-1H-pyrazole (10 g, 88 mmol) and 5% palladium on Al2O3 (1 g) in a mixture of ethanol (150 mL) and 50% aqueous HBr (50 mL) was shaken in a Par apparatus under hydrogen (10 psi) for 36 h. The mixture was filtered and the catalyst washed with ethanol. The filtrate was concentrated in vacuo to give a white solid. This solid was suspended in 10 mL of ethanol. After swirling the flask for 5 min, ether was added to complete the crystallization. The solid was filtered, was washed with ether and dried under high vacuum to afford 5-bromo-1H-pyrazol-4-amine, HBr (18.1 g, 84% yield) as a white solid: mp 248 C. dec; 1H NMR (400 MHz, DMSO-d6) delta 11.47 (s, 1H), 10.00 (s, 1H), 7.79 (s, 1H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2075-46-9.

5334-40-7, 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. 5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic acid, A new synthetic method of this compound is introduced below.

Add 6.31 kg of raw material to a 100 L reactor, N,N-dimethylformamide (45 L), carbodiimide (6.59 kg), 1-hydroxybenzotriazole (4.65 kg), stirred for 0.5 h, The ice water bath was cooled to 0 to 10 C, and the starting material 1 (4.5 kg) was added in portions, and then the temperature was raised to 20-25 C, and the reaction was stirred for 16 hours. The reaction solution was added to 270 L of water, and a solid was precipitated, suction filtered, washed, and separated, and the organic phases were combined and dried

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

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. 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., 5932-27-4

Description 14; Ethyl 1 -{[4-(5-{3-chloro-4-[(1 -methylethyl)oxy]phenyl}-1 ,2,4-oxadiazol-3- yl)phenyl]methyl}-1H-pyrazole-3-carboxylate (D14); [4-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1 ,2,4-oxadiazol-3-yl)phenyl]methanol (D13) (200 mg) and ethyl 1 H-pyrazole-3-carboxylate (D1 ) (85 mg) were dissolved in toluene (4.6 ml) under an Ar atmosphere and treated with tributylphosphine (152 mul). After stirring for 5 minutes 1 ,1′-azobis(N,N-dimethylformamide) (105 mg) was added and stirring continued overnight. The reaction mixture was then filtered, washing with toluene, and evaporated to dryness. The residue was purified by flash chromatography on silica, eluting with a 0-100 percent EtOAc in pentane to give the undesired isomer (86 mg) and the title compound (108 mg) in poor purity. deltaH (CDCI3, 400MHz): 1.42 (3H, t), 1.45 (6H, d), 4.43 (2H, q), 4.72 (1 H, quintet), 5.48 (2H, s), 6.87 (1 H, d), 7.06 (1 H, d), 7.36 (2H, d), 7.41 (1 H, d), 8.05 (1 H, dd), 8.14 (2H, d), 8.23 (1 H, d). MS (ES): C24H23CIN4O4 requires 466.92; found 467 (M+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.