Category: imidazoles-derivatives

Some common heterocyclic compound, 72-40-2, name is 5-Amino-1H-imidazole-4-carboxamide hydrochloride, molecular formula is C4H7ClN4O, 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: imidazoles-derivatives

(e) 4-({[3-Ethoxy-4-(2-ethoxyethoxy)pyridin-2-yl]methyl}amino)-lH-imidazole-5- carboxamide; NaCNBH3 (0.046 g, 0.73 mmol) was added in portions to a stirred solution of 5-amino-4- imidazolecarboxamide hydrochloride (0.150 g, 0.92 mmol) and 3-ethoxy-4-(2- ethoxyethoxy)pyridine-2-carbaldehyde (0.220 g, 0.92 mmol, obtained from Example 4(d)) in MeOH (1.5 mL) at r.t. over 10 minutes. The reaction mixture was stirred at r.t. for 2 days. The mixture was filtrated and the filtrate was evaporated in vacuo to give a crude of the title compound in quantitative yield. MS (ESI) m/z 364 (M +1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 72-40-2, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2007/120098; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 5805-52-7, name is 1H-Benzimidazole-2-carboxamide, belongs to imidazoles-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 5805-52-7, SDS of cas: 5805-52-7

To a solution of 9 (3.0 g, 18.6 mmol) in THF (70 mL) wasadded Lawesson?s reagent (7.5 g, 18.6 mmol). The resulting solution was stirred at 66 C for 5 h. Aftercomplete conversion of the starting material, the reaction mixture was concentrated in vacuo and theresidue was redissolved in DCM (500 mL), the solution was washed with saturated NaCl solutionthree times, dried over anhydrous sodium sulfate, concentrated and purified by flash silica gel columnchromatography (DCM:MeOH = 100:1) to obtain 10 as yellow solid in 61.2% yield. LC-MS m/z: 178.2[M + H]+.

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Reference:
Article; Wang, Shuxiang; Guan, Lihong; Zang, Jie; Xing, Kun; Zhang, Jian; Liu, Dan; Zhao, Linxiang; Molecules; vol. 24; 7; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, molecular formula is C19H13BrN2, 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. SDS of cas: 2620-76-0

Example 1.3.3 1-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazole (10): A mixture of Compound 9 (0.70 g, 2 mmol), bis(pinacolate)diborane (0.533 g, 2.1 mmol), 1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium (Pd(dppf)Cl2) (0.060 g, 0.08 mmol) and anhydrous potassium acetate (0.393 g, 4 mmol) in 1,4-dioxane (20 mL) was heated at 80 C. under argon overnight. After cooling to r.t., the whole mixture was diluted with ethyl acetate (80 mL) then filtered. The solution was absorbed on silica gel, then purified by column chromatography (hexanes/ethyl acetate 5:1 to 3:1) to give a white solid (Compound 10) (0.64 g, in 81% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2620-76-0, its application will become more common.

Reference:
Patent; Nitto Denko Corporation; US2012/15998; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 360-97-4, name is 4-Amino-1H-imidazole-5-carboxamide, belongs to imidazoles-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 360-97-4, Formula: C4H6N4O

Example C.30 4-Trifluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carboxylic acid; 1) A stirred solution of commercially available 5-amino-1H-imidazole-4-carboxamide (25 g, 198 mmol) in methanesulfonic acid (107 ml) and ethanol (400 ml) was stirred at reflux conditions for 12d, evaporated and water (300 ml) was added. While stirring and cooling (ice/water) sodium hydroxide solution (32%) was added until pH=6 was reached. The water layer was saturated with sodium chloride and extracted with ethyl acetate (3¡Á200 ml). The combined organic layers were dried (MgSO4), evaporated and the crude product purified crystallization (ethyl acetate/ethanol) to yield 5-amino-1H-imidazole-4-carboxylic acid ethyl ester (13.7 g, 45%) as a light brown solid. MS (EI) 155.1 [(M)+]; mp 178 C. 2) A mixture of 4,4,4-trifluoro-1-(4-trifluoromethyl-phenyl)-butane-1,3-dione (10.0 g, 35.2 mmol) and 5-amino-1H-imidazole-4-carboxylic acid ethyl ester (5.0 g, 32.2 mmol) in acetic acid (120 ml) was refluxed for 24 h and evaporated. The crude product was further purified by column chromatography on silica gel (ethyl acetate/heptane) and crystallization (diethyl acetate/hexane) to yield 4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carboxylic acid ethyl ester (5.65 g, 43%) as a yellow solid. MS (EI) 403.1 [(M)+]; mp 243 C. 3) A mixture of 4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carboxylic acid ethyl ester (5.6 g, 13.9 mmol), 2M potassium hydroxide solution (111 ml) and water (55 ml) was stirred at room temperature for 5h, cooled (ice-water), and acetic acid (30 ml) was added. The mixture was evaporated, acetic acid (150 ml) was added and the stirred solution was heated under reflux conditions for 20 min. The reaction mixture was evaporated, water (150 ml) was added followed by extraction with ethyl acetate (2¡Á300 ml). The combined organic layers were washed with brine (2¡Á150 ml), dried (MgSO4) and evaporated. The crude product was further purified by cholumn chromatography on silica gel (ethyl acetate/heptane 1:1) to yield 4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carboxylic acid (1.93 g, 37%) as a yellow solid. MS (ISN) 374.3 [(M-H)-]; mp 231 C.

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-Amino-1H-imidazole-5-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; McArthur, Silvia Gatti; Goetschi, Erwin; Wichmann, Juergen; Woltering, Thomas Johannes; US2007/72879; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 5395-50-6, name is 1,3,4,6-Tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, belongs to imidazoles-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 5395-50-6, Quality Control of 1,3,4,6-Tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

1 ,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo [4,5-d]imidazole-2,5(1H,3H)-dione (3 g, 11.4 mmol) in tetrahydro-4-pyranol (11 ml, 114 mmol) was dissolved. Then, 0.15 ml nitric acid (65%) was added to the solution and the mixture was heated at 60 C. for 16 hours. Afier the reaction was over, the reaction liquid was cooled and iN NaOH was added around pH 7. Around 100 ml ethyl acetate was used to extract with mixture and the organic phase was washed by saturated NaC1(aq) solution for 2 times. After being dried by Na2504, the solvent was removed. The crude compound was purified by flash chromatography (MC/acetone). The product was obtained colorless viscous oil. ?H NMR (600 MHz, DMSO-d6): oe (ppm) 5.57 (s, 2H), 4.84 (m, 8H), 3.78 (m, 8H), 3.57 (m, 4H), 3.29 (m, 8H), 1.82 (m, 8H), 1.40 (m,8H)

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, 1,3,4,6-Tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Rohm and Haas Electronic Materials LLC; Rohm and Haas Electronic Materials Korea Ltd.; Grandbois, Matthew; Kim, Myung Yeol; Ryu, Eui Hyun; Sim, Jae Hwan; Jang, Min Kyung; Lee, Jung-June; (17 pag.)US2017/59991; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, molecular formula is C4H3N3, 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. HPLC of Formula: C4H3N3

Example 4 Production of 1-(1H-imidazol-4-yl)-1-butanone A solution of 4-cyanoimidazole (2 g, 21.4 mmol) in THF (25 ml) was added dropwise to a solution (68.5 mL, 68.5 mmol, 3.2 equivalents) of 1 M n-propyl magnesium bromide in THF at 0to 10¡ãC under a nitrogen atmosphere. The mixture was stirred at 15 to 25¡ãC for 4 h. Water (20 ml) and 10percent aqueous sulfuric acid solution (45 ml) were successively added dropwise, and the mixture was stirred at 1 h. A 30percent aqueous sodium hydroxide solution was added dropwise to adjust the pH to 8. After partitioning, the aqueous layer was extracted with ethyl acetate (15 ml * 2). The organic layer was combined, and the mixture was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, and concentrated under reduced pressure. The concentration residue was broken up with n-hexane (12 ml), and the crystals were collected by filtration and washed with n-hexane. The crystals were dried in vacuo (40¡ãC) to give 1-(1H-imidazol-4-yl)-1-butanone (2.45 g, yield 83percent). 1H-NMR (CDCl3): delta0.90(3H, t, J=7.4Hz), 1.60(2H, q, J=7.3Hz), 3.34(2H, q, J=7.1Hz), 7.77(1H, s), 7.85(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 57090-88-7, its application will become more common.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1193258; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, belongs to imidazoles-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 68282-53-1, COA of Formula: C5H6N2O

COMPOUND 12.1.40: N,N-DIETHYL-4-[6-METHOXY-2-[(5-METHYL-1H- IMIDAZOL-4-YL) METHYLI-‘7-(2-MORPHOLIN-4-YLETHOXY)-1, 2, 3, 4- TETRAHYDROISOQUINOLIN-1-YLBENZAMIDE; To a solution of INTERMEDIATE 7.1. 3 (22 mg, 0.0471 mmol) in anhydrous 1,2- dichloroethane (1 mL) was added 4-methyl-lH-imidazole-5-carbaldehyde (10 mg, 0.0909 mmol, 1.9 eq). After stirring for 5 min, sodium triacetoxyborohydride (29.8 mg, 0.141 mmol, 3 eq) was added in one lot. The reaction mixture was stirred at RT for 48hr, then quenched with saturated aqueous sodium bicarbonate (0.8 mL) and extracted with dichloromethane (2 x 10 mL). Excess aldehyde was removed by stirring the extracted dichloromethane with polymer supported hydrazine for 2 hr. The polymer was filtered off and the filtrate was concentrated and dried under vacuum. Product was purified by flash chromatography, using Si02 column with MeOH/DCM (10: 90) gave 24.6 mg (0. 0438 mmol, 93%) of COMPOUND 12.1. 40 as oil. 1H NMR (500 MHz, CDC13) : No. 1.15 (br s, 3H), 1.28 (br s, 3H), 2.13 (s, 3H), 2.51 (m, 4H), 2.58 (m, 1H), 2.69 (m, 2H), 2.75 (m, 1H), 2.90 (m, 1H), 3.08 (m, 1H), 3.30 (br s, 2H), 3.40 (m, 1H), 3.55 (br s, 2H), 3.60 (m, 1H), 3.69 (m, 4H), 3.70 (s, 3H), 3.85-3. 95 (m, 2H), 4.58 (s, 1H), 6.23 (s, 1H), 6.62 (s, 1H), 7. 28-7. 34 (m, 4H). 13C NMR (125 MHz, CDC13) : 6 10. 96,13. 10,14. 10,27. 96,39. 69,43. 66,46. 56,49. 03, 50.84, 54.26, 56.13, 67.08, 67.35, 111. 81, 114.92, 126.59, 127.94, 128.96, 129.92, 132.83, 136.37, 145.20, 146.72, 148.79, 171.47. (+) LRESIMS m/z 562 (M+H) +.

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.

Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 103057-10-9, These common heterocyclic compound, 103057-10-9, name is 4-(Chloromethyl)-1-trityl-1H-imidazole, 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 1 STR49 To a solution of diisopropylamine (1.078 mL) in anhydrous THF (7 mL) was added n-butyllithium (3.08 mL; 2.5M) dropwise at 0 C. The resulting solution was stirred at 0 C. for 40 minutes and then was cooled to -23 C. To this mixture was added N-methyl-2-piperidinone (0.80 mL) (1.) the mixture was stirred at -23 C. for 0.5 hour, and then at -78 C. for 1 hour. To the above mixture was added dropwise a solution of 4-chloromethyl-N-trityl-imidazole (2.70 g) STR50 in anhydrous THF (14 mL). The mixture was stirred at -78 C. for 4 hours and then was allowed to warm up to room temperature slowly overnight (16 hours). Water and ethyl acetate were added to the mixture, the resulting mixture was shaken vigorously, the layers separated, and the aqueous layer was extracted with ethyl acetate several times. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated to give the crude product, which was purified by flash chromatography (1% to 2% of ammonia saturated methanol in CH2 Cl2) to give 2 (1.58 g; 52% yield).

The synthetic route of 103057-10-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schering Corporation; US5807872; (1998); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, belongs to imidazoles-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 41716-18-1, COA of Formula: C5H6N2O2

To a solution of N1 -(2-chloro-6-phenylpyrimidin-4-yl)cyclohexane- 1,3 -diamine (221 mg, 0.73 mmol) in a mixed solvent of tetrahydrofuran (4 mL) and dimethyl sulfoxide (1 mL) were added N,N-diisopropylethylamine (0.11 mL, 0.7 mmol) and 1-methyl-1H-imidazole-4-carboxylic acid (184 mg, 1.46 mmol). The mixture was stirred at rt for 10 mm, then HATU (555 mg, 1.46 mmol) was added. The resulting mixture was stirred at rt for 3 h. To the reaction mixture was added water (10 mL), and the resulting mixture was extracted with ethyl acetate (10 mL x 3). The combined organic layers were washed with saturated brine (30 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound as a colorless solid (180 mg, 60percent).MS (ESI, pos.ion) m/z: 411.2 [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, 1-Methyl-1H-imidazole-4-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; REN, Qingyun; TANG, Changhua; LIN, Xiaohong; YIN, Junjun; YI, Kai; (270 pag.)WO2017/97234; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 1792-40-1, name is 2-Methyl-5-nitro-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-Methyl-5-nitro-1H-benzo[d]imidazole

General procedure: Conventional Method. A solution of KOH (0.01mol) in water (20 mL) and CS2 (0.01 mol) was added to solution of 4a-d (0.01 mol) in ethanol (20 mL) and then, the mixture was refluxed for 4 hours. After the reaction was completed, monitored by TLC (Ethyl acetate: Hexane, 3:1), the mixturewas cooled down to room temperature and neutralized with diluted HCl (4N). The mixture was left to cool down and the precipitated product was filtrated, washed with H2O andrecrystallized from ethanol. Microwave Method. A solution of 4a-d (0.01 mol) in ethanol(10 mL) and KOH (0.01 mol) in water (5 mL) were taken in a microwave process vial. Then, the mixture was heated under microwave irradiation 300 Watt at 100 C, with stirring and air-jet cooling for 5 min. After the mixture was cooled down, CS2 (0.01 mol) was added to the mixture and then, heated again 300 Watt at 100 C. Completion of reaction was achieved in 10 min. as indicated by TLC. Then, the mixture was neutralized with 4 N HCl and left to cool. The precipitated product was filtrate, washed with H2O and recrystallized from ethanol. 5-[(2-Methyl-5(6)-nitro-1H-benzimidazole-1-yl)methyl]-1,3,4-oxadiazole-2-thiol (5a) M.p. 249-250 C. IR (KBr), nu/cm-1: 3021, 2968, 2698, 1618,1518, 1343, 1250, 1145. 1H-NMR (DMSO-d6, 200 MHz) delta: 14.22 (s, 1H, SH), 8.44 (s, 1H, Ar-H), 8.18 (d, 1H, Ar-H,J=8.8), 7.86 (d, 1H, Ar-H, J=8.8), 5.71 (s, 2H, CH2), 2.42 (s,3H, CH3) ppm. 13C NMR (DMSO-d6, 50 MHz) delta: 14.29, 43.24, 111.38, 115.09, 118.64, 136.14, 142.14, 143.66,157.43, 159.50, 178.73 ppm. Anal. Calcd. For C11H9N5O3S: C, 45.36; H, 3.11; N, 24.04; S, 11.01; Found: C, 45.38; H,3.13; N, 24.05; S, 11.02; ESI-MS: m/z: 292 [M]+.

The synthetic route of 1792-40-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kahveci, Bahittin; Sosan, Nesibe; Mentese, Emre; Yilmaz, Fatih; Revue Roumaine de Chimie; vol. 58; 6; (2013); p. 511 – 515;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem