Tag: M.W=100-200

Synthetic Route of 5955-72-6, A common heterocyclic compound, 5955-72-6, name is 2-Chloro-6-nitro-1H-benzo[d]imidazole, molecular formula is C7H4ClN3O2, 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.

Step 3. NaH (60%) in mineral oil was added portion-wise to a stirred suspension of 2-chloro-5- nitro-lH-benzo[d] imidazole (A/1482/81/1) in dry DMF at 0 C under a nitrogen atmosphere The ice-bath was removed, and the reaction mixture was stirred at RT. After 0.5 h the mixture was cooled to 0 C, and 2-trimethylsilylethyoxymethyl chloride (0.38 mL) was added drop-wise. The ice-bath was removed, and the resulting reaction mixture was stirred at RT. After lh, UPLC showed complete conversion. A saturated ammonium chloride solution and EA were added, the organic phase was separated, washed with water, dried over sodium sulfate and the solvent removed under vacuum. The crude material was purified by FC on silica (Snap 100, eluting with Cy EA from 100/0 to 80/20) to give the desired product A/1482/82/1 as yellow oil. Step 4. To a solution of methyl glycolate in dry THF (8 ml) cooled at 0 C was added NaH (60%) in mineral oil. The reaction was stirred at room temperature for 2h. The suspension was cooled at 0 C and a solution of A/1482/82/1 was added dropwise. The reaction mixture was stirred at room temperature for 16h. UPLC showed ~70% reaction completion, and another 1.1 eq of NaH was added. After stirring for 16h, UPLC showed formation of side products. The reaction was stopped, and S. NH4C1 and EtOAC were added. The organic phase was separated, dried and evaporated to give a crude product, which was then purified by silica column (CyHex to CyHex: EtOAc= 85:15). The product named A/1482/83/1 was recovered with a 50% of purity grade (by NMR), with the UPLC retention time of the impurity that same as that of the desired product. Step 5. To a stirred solution oh the A/1482/83/1 cooled to 0 C in THF, a solution of LiOH in water was added dropwise. The mixture was then stirred at room temperature for 2h. UPLC showed complete conversion. The solvent was evaporated under vacuum. The residue was portioned between water and EtOAc, the organic phase was separated and discarded. The water phase was evaporated to give the desired product as the corresponding lithium salt A/1482/84/1.

The synthetic route of 5955-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE GENERAL HOSPITAL CORPORATION; ZAHLER, Robert; WESTER, Ronald Thure; BRICKNER, Steven Joseph; WO2014/176258; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2466-76-4, name is 1-(1H-Imidazol-1-yl)ethanone, 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 2466-76-4, HPLC of Formula: C5H6N2O

General procedure: Nucleoside/nucleotide (2; 100 mM) and N-acetyl imidazole (1a;10 equiv) were dissolved in water (pH 8; adjusted with 4 MNaOH). The solution was incubated at r.t. for 4 h, and NMR spectra were periodically acquired. The product was purified byreverse-phase (C18) flash coumn chromatography (eluted at pH4 with 100 mM NH4HCO2/MeCN = 98:2 to 80:20). The fractions containing 5 were lyophilised to yield a white powder.

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-(1H-Imidazol-1-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fernandez-Garcia, Christian; Powner, Matthew W.; Synlett; vol. 28; 1; (2017); p. 78 – 83;,
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These common heterocyclic compound, 492-98-8, name is 1H,1’H-2,2′-Biimidazole, 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. Computed Properties of C6H6N4

General procedure: A mixture of H2ATIBDC (0.084 g, 0.150 mmol) and NaOH (0.3 ml, 0.5 mol/l) was dissolved in water (5 ml) and then an aqueous solution of CdCl2¡¤2.5H2O (0.034 g, 0.150 mmol) in water (5 ml) was added whilst stirring. To this solution biim (0.008 g, 0.050 mmol) in methanol (5 ml) was added and then filtered. The compound was obtained from the filtrate with a 68% yield based on H2ATIBDC.

The synthetic route of 1H,1’H-2,2′-Biimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Lei; Wei, Yan; Zhong, Ya-Qiang; Chang, Yan; Meng, Qing-Hua; Ng, Seik Weng; Zhang, Kou-Lin; Inorganica Chimica Acta; vol. 435; (2015); p. 7 – 15;,
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Synthetic Route of 4857-06-1, 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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 2-Chloro-1H-benzoimidazole (3.04 g, 20 mmol) was dissolved in dry DMF (15 mL) at 0 C, to the solution was added NaH (0.91 g, 22.7 mmol), and the mixture was stirred for 1 h at 0 C, then halide (21.6 mmol) was added. The mixture was stirred overnight at room temperature and was poured into water (50 mL) and stirred for 1 h, filtrated, washed with water and dried to afford 4a-d.

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, 2-Chloro-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Luo, Yu; Xiao, Feng; Qian, Shijing; Lu, Wei; Yang, Bo; European Journal of Medicinal Chemistry; vol. 46; 1; (2011); p. 417 – 422;,
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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

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: 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) +.

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Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
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;,
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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;,
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