Author: Jessica.F

Application of 16042-25-4, These common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, 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.

[00535] lH-Imidazole-2-carboxylic acid { 3-r4-(6-cyclohexylamino-9H-purin-2-ylamino)-3-methylphenoxylpropyl|amide (C14): Diisopropylethyl amine (0.10 g, 0.81 mmol) was added to a solution of lH-imidazole-2-carboxylic acid (0.025 g, 0.22 mmol), N- 2-[4-(3-aminopropoxy)-2-methyl-phenyl]-N-6-cyclohexyl-9H-purine-2,6-diamine (0.08 g, 0.20 mmol), EDCI (0.046 g, 0.24 mmol), and HOBt (0.037 g, 0.24 mmol) in DMF (1.0 mL), and the resulting mixture was stirred overnight at ambient temperature. The solvent was removed and the crude material was purified by reverse-phase HPLC to provide compound (Table 1, C14).

The synthetic route of 16042-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MYRIAD PHARMACEUTICALS, INC.; KUMAR, Dange, Vijay; MCALEXANDER, Ian, A.; BURSAVICH, Matthew, Gregory; HOARAU, Christophe; SLATTUM, Paul, M.; GERRISH, David, A.; LOCKMAN, Jeffrey, W.; JUDD, Weston, R.; SAUNDERS, Michael; PARKER, Daniel, P.; ZIGAR, Daniel, Feodore; KIM, In, Chul; WILLARDSEN, J., Adam; YAGER, Kraig, M.; SHENDEROVICH, Mark, D.; WILLIAMS, Brandi, L.; TARDIF, Keith, D.; WO2010/111406; (2010); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

Example No. 302Preparation of 5- (3 , 4 -dihydro-2H-benzo [b] [1,4] oxazin-6-yl) -N- (2-methyl-lH-benzo [d] imidazol-5-yl) -lH-pyrazolo [4,3- d] pyrimidin-7-amine6- (7-chloro-2- (4 -methoxybenzyl) -2H-pyrazolo [4 , 3-d] pyrimidin-5- yl) -2H-benzo [b] [1 , 4] oxazin-3 (4H) -one (0.16 mmol) and 2 -methyl – lH-benzo [d] imidazol-5-amine (0.3 mmol 2 eq.,) were suspended in MeOH (dry, 3mL) in a microwave vial (2-5mL) , HC1 in dioxane (4M, 3 drops) was added. The reaction mixture was irradiated in a microwave reactor for 5 min at 140C. The reaction mixture was evaporated and used without further purification. The reaction mixture was dissolved in THF (dry) LiAlH4 powder was added (excess, 2 by 2 eq) until completion of reaction is observed (by LCMS) . The reaction was quenched with water (lmL per gram LiAlH4) , then NaOH (ca. 15% aq. , lmL per g LiAlH4) , water (3mL per gram LiAlH4) . The mixture was filtered, washed with THF, MeOH, MeCN (ca. 10ML each) . The residue was dissolved in TFA (3mL) . The reaction mixture was irradiated in a microwave reactor for 5 min at 140 C. The reaction mixture was concentrated and purified by semi-preparative HPLC-MS and freeze dried from water/t-BuOH 4/1. exact mass: 398.1840 g/molHPLC-MS: analytical method Lrt: 3.09 min – found mass: 399 (m/z+H)

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 29043-48-9.

Reference:
Patent; ORIGENIS GMBH; ALMSTETTER, Michael; THORMANN, Michael; TREML, Andreas; TRAUBE, Nadine; WO2012/143144; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-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 152628-03-0, name: 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid

1.2 kg of isoamyl alcohol was added to the reaction flask.Add 2-n-propyl-4-methyl-6-carboxybenzimidazole (400 g, 1.83 mol) and stir.Methanesulfonic acid (176 g, 1.83 mol, 1.0 eq) was added and N-methyl-phenylenediamine hydrochloride (360 g, 1.85 mol) was added.The temperature was raised to 130-135 C to reflux and the reaction was carried out for at least 18 hours until no significant moisture was separated. After the reaction is completed, cool to about 70 C,Add 2000 ml of water, stir, adjust the pH to 6~7 with 30% NaOH solution, stir and cool to 20~25 C after completion, and filter to obtain the product, the yield is 93.0%, and the HPLC purity is 99.6%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Weihai Disu Pharmaceutical Co., Ltd.; Disha Pharmaceutical Group Co., Ltd.; Li Xinfa; Cui Dapeng; (6 pag.)CN104974096; (2019); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 496-46-8, 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. 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, This compound has unique chemical properties. The synthetic route is as follows.

Example 2: Synthesis of cucurbituril homologues; [27] 3 g of paraformaldehyde was added to 5.68g of glycolurils of formula 9 and 20 mL of a 9M sulfuric acid was added thereto. Then, a 800W microwave was irradiated to the reaction mixture for 45 seconds. [28] The reaction solution was recrystallized with acetone and methanol to thereby synthesize and separate four cucurbituril homologues, CB[5], CB[6], CB[7], and CB[8 ], as represented by formula 1 where X is 0, Rand R are H, and n is 5,6, 7, and 8, respectively. The yields of CB[5], CB[6], CB[7], and CB[8] were 15%, 45%, 20%, and 15%, respectively. [29] CB [5]:¹ H (500 MHz, D 2O/CF CO DID SO 4 (1:1:0.15)): No. 4.43 (d, J = 15.5 Hz, 10H), 5.65 (s, 10H), 5.85 (d, J =15.5 Hz, lOH). [30] CB [6]:¹ H (500 MHz, D 2 O/CF 3CO2 DID 2 SO 4 (1: 1:0.15)): No. 4.35 (d, J = 15.5 Hz, 12H), 5.61 (s, 12H), 5.69 (d, J =15.5 Hz, 12H). [31] CB [7]:¹ H (500 MHz, D 2 O/CF 3CO2 DID 2 SO 4 (1: 1:0.15)): No. 4.29 (d, J = 15.5 Hz, 14H), 5.60 (s, 14H), 5.91 (d, J =15.5 Hz, 14H). [32] CB [8]:¹ H (500 MHz, D 2 O/CF 3CO2 DID 2 SO 4 (1: 1:0.15)): No. 4.28 (d, J = 15.5 Hz, 16H), 5.60 (s, 16H), 5.93 (d, J =15.5 Hz, 16H).

The chemical industry reduces the impact on the environment during synthesis Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; POSTECH ACADEMY-INDUSTRY FOUNDATION; WO2005/103053; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1615-14-1,Some common heterocyclic compound, 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, molecular formula is C5H8N2O, 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.

The mixture containing 1.0 g (8.9 mmol) of 1-(2-hydroxyethyl)imidazole and 3.59 g (9.8 mmol) of 1-octadecyl bromide dissolved in 10 mL of acetonitrile was boiled with reflux condenser for 24 h. The precipitate formed during cooling was filtered, purified by recrystallization from ethyl acetate and dried under vacuum. Yield: 3.00 g (69%). Mp=56-58 C. IR-spectrum (KBr), cm-1: 3325, 3140, 3080, 2915, 2850, 1565, 1472,1378, 1165,1071, 871, 721. 1H NMR spectrum, 400 MHz (CDCl3), delta,ppm, J/Hz: 0.87 t (3H, J=7.0), 1.24-1.32m (30 H), 1.89-1.92m (2 H),3.98 t (2H, J=4.27), 4.26 t (2H, J=7.6), 4.53 t (2H, J=4.90), 7.31 s(1 H), 7.63 s (1 H), 9.73 s (1 H). ESI MS, m/z: 365.5 [M-Br]+.Calculated, %: C23H45 N2 OBr: C 62.00; H 10.18; N 6.29; Br 17.93;found, %: C 61.75; H 10.43; N 6.22; Br 17.58.

The synthetic route of 1615-14-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kuznetsova, Darya A.; Gabdrakhmanov, Dinar R.; Lukashenko, Svetlana S.; Voloshina, Alexandra D.; Sapunova, Anastasiia S.; Kashapov, Ruslan R.; Zakharova, Lucia Ya.; Chemistry and Physics of Lipids; vol. 223; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 2466-76-4, The chemical industry reduces the impact on the environment during synthesis 2466-76-4, name is 1-(1H-Imidazol-1-yl)ethanone, I believe this compound will play a more active role in future production and life.

Step Three; N-((1S, 2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-{[(4S)-6- hydroxy-3, 4-dihydro-2H-chromen-4-yl] amino} propyl) acetamide; OH H H OH H H2N N N-N 2HCl \ 1. 2 equiv. acetylimidazole 2HCl ~ + l 1. 2equiv. acetinidazole 11 41 A 2. K2CO3, MeOH, H20/==\ F HOpercent F HO/ F F To a solution of the product from step 2 (200 mg, 0.43 mmol) in methylene chloride (5 mL) was added triethylamine (217 mg, 2.15 mmol) followed by 1-acetylimidazole (95 mg, 0.86 mmol). The reaction mixture was stirred at room temperature for 16 h. The solvent was removed under reduced pressure. The residue was dissolved in methanol (6 mL) and water (3 mL) and treated with potassium carbonate (300 mg, 2.17 mmol). The reaction mixture was stirred at room temperature for 2 h. The solvent was removed under reduced pressure. The residue was acidified with 1N hydrochloric acid and extracted with ethyl acetate (3 x 50 mL). The combined extracts were washed with saturated sodium chloride, and dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 0-5percent methanol/methylene chloride provided the desired product (85 mg, 49percent) as a white foam.

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:
Patent; ELAN PHARMACEUTICALS, INC.; PHARMACIA & UP JOHN COMPANY; WO2005/95326; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 492-98-8, 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.

Example 4: Synthesis of (tetrakis(2-(2,4-difluorophenyl)pyridinato)(mu-biimidazolyl) diiridium(III), Abbreviation; [Ir(dfppy)2BIm]2) [0243] [0244] Under argon atmosphere, into a 250 mL Schlenk flask equipped with a stirrer were placed 486 mg (0.40 mmol) of di-mu-chloro-tetrakis(2-(2,4-difluorophenyl)pyridinato) diiridium(III), 54 mg (0.40 mmol) of 2,2′-biimidazole and 80 ml of tetrahydrofuran. And then, the mixture was stirred at room temperature for 1 hour. Subsequently, 111 mg (0.84 mmol) of tert-butoxy potassium (t-BuOK (85 wt% product)) was added to the mixture, and the mixture was reacted under stirring at room temperature for 2 hours. After the completion of the reaction, the reaction liquid was concentrated, and then methylene chloride, water and a saturated aqueous solution of ammonium chloride were added to the resultant concentrate until pH became 7, and the organic phase was separated from the water phase. The resultant organic phase was dried with sodium sulfate, and filtered, and then the filtrate was concentrated. And then, the resultant concentrate was washed with hexane, to provide 441 mg of binuclear iridium complex (1) as a yellow solid. (Isolation yield: 86 %) [0245] The obtained binuclear iridium complex (1) was a mixture of two different types of isomers, and the abundance ratio was 60:40. The binuclear iridium complex obtained as the main product (60 %) was referred to as “binuclear iridium complex (1a)” and the binuclear iridium complex obtained as the secondary product (40 %) was referred to as “binuclear iridium complex (1b)” [0246] Additionally, the binuclear iridium complex (1) was a novel compound, which had the following properties: [0247] 1H-NMR (400MHz, C4D8O, delta (ppm)); Binuclear iridium complex (1a); 8.17 (d, 4H), 8.13-8.12 (m, 4H), 7.79-7.75 (m, 4H), 7.91-7.15 (m, 4H), 6.49-6.42 (m, 4H), 6.22 (s, 4H), 5.84-5.81 (m, 4H) Binuclear iridium complex (1b); 8.24 (d, 4H), 7.85-7.81 (m, 4H), 7.74-7.72 (m, 4H), 6.95-6.91 (m, 4H), 6.49-6.42 (m, 4H), 6.24 (s, 4H), 5.77-5.74 (m, 4H) FD-MS (M/Z): 1276 (M+)

Statistics shows that 1H,1’H-2,2′-Biimidazole is playing an increasingly important role. we look forward to future research findings about 492-98-8.

Reference:
Patent; Ube Industries, Ltd.; FUJIMURA, Osamu; FUKUNAGA, Kenji; IWASA, Takafumi; TANAKA, Yasuhiro; FUJITA, Harunori; MURAKAMI, Tadashi; HONMA, Takashi; MACHIDA, Toshikazu; KASHIHARA, Natsuko; EP2647642; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 152628-02-9,Some common heterocyclic compound, 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, molecular formula is C19H20N4, 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.

General procedure: A solution of an appropriate benzimidazole (5.03mmol) and NaH (0.12g, 5.53mmol, 60%) in 100mL anhydrous THF was stirred for 30minat 50C. After cooling to rt, a mixture of an appropriate bromide (6.04mmol) in anhydrous THF (50mL) was added dropwise to the solution. The solution was stirred for 3hat 50C. Then the resulting mixture was poured into 30mL ice water, and extracted with ethyl acetate (50mL×3). The combined organic layer was dried over MgSO4. After filtration, the solvent was removed under reduced pressure and the residue was purified by CC to give the product as white solid 4.1.7.8 [5-[[2-Propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)benzimidazole-1-yl]methyl]-1H-indol-1-yl](phenyl)methanone (15c) 15c was prepared by following the above general procedure. Yield: 85.6%. MP: 214-217 C. 1H NMR (400 MHz, CDCl3): delta 8.35 (d, 1H), 7.86 (s, 1H), 7.78 (d, 2H), 7.60 (t, 2H), 7.54 (t, 2H), 7.43 (s, 2H), 7.34 (d, 2H), 7.31 (t, 2H), 7.28 (d, 1H), 6.73 (d, 1H), 5.68 (s, 2H), 3.74 (s, 3H), 2.94 (t, 2H), 2.78 (s, 3H), 1.85 (m, 2H), 1.04 (t, 3H). MS (ESI): [M + H]+ calcd 538.3; found 538.3.

The synthetic route of 152628-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhu, Weibo; Bao, Xiaolu; Ren, He; Da, Yajing; Wu, Dan; Li, Fuming; Yan, Yijia; Wang, Li; Chen, Zhilong; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 161 – 178;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 934-32-7,Some common heterocyclic compound, 934-32-7, name is 1H-Benzo[d]imidazol-2-amine, molecular formula is C7H7N3, 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.

General procedure: In a round-bottom flask, catalyst 1 {[HIMI]C(NO2)3}(1.0 mol%, 2.2 mg) was added to a mixture of the corresponding aromatic aldehyde (1.0 mmol), 2-aminobenzimidazole(1.0 mmol, 133 mg), and malononitrile (1.0 mmol,66 mg). The obtained mixture was stirred magnetically at50 C under solvent-free conditions for the appropriate time. After completion of the reaction, as identified by TLC(n-hexane/EtOAc: 5/3), EtOAc (10 mL) was added, and the mixture was stirred and refluxed for 10 min. Then, the resulting solution was washed with water (10 mL). Separation of the phases led to the crude product in the EtOAc phase while catalyst 1 was soluble in water. The organic phase was dried (MgSO4) and the solvent evaporated to afford the corresponding crude product which was purified via recrystallization from ethanol/water (10:1).

The synthetic route of 934-32-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yarie, Meysam; Zolfigol, Mohammad Ali; Baghery, Saeed; Khoshnood, Abbas; Alonso, Diego A.; Kalhor, Mehdi; Bayat, Yadollah; Asgari, Asiye; Journal of the Iranian Chemical Society; vol. 15; 10; (2018); p. 2259 – 2270;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 26663-77-4 as follows. Application In Synthesis of Methyl benzimidazole-5-carboxylate

To a solution of methyl 1H-benzo[d]imidazole-5-carboxylate (0.90 g, 5.1 mmol) in DMF(20 ml) was added NaH (0.25 g, 6.2 mmol), and the reaction mixture was stirred at room temperature for 30 mm. Then (2-(chloromethoxy)ethyl)trimethylsilane (0.94 g, 5.6 mmol) wasadded and the reaction mixture was stirred at room temperature for 2 hours. When LCMS showed that the reaction completed, the reaction mixture was diluted with EtOAc (100 mL), washed with H20 (100 mL x 2) and brine (100 mL), dried over Na2504 and concentrated under reduced pressure to afford crude product as an oil, which was purified by column chromatography on silica gel (eluted with petroleum ether/EtOAc = 1:1) to afford mixture ofmethyl 1 -((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d]imidazole-5-carboxylate and methyl 1- ((2-(trimethylsilyl)ethoxy) methyl)- 1 H-benzo [d] imidazole-6-carboxylate as an oil. LC/MS (m/z): 307 (M+H).To a solution of LiA1H4 (0.30 g, 7.8 mmol) in THF (20 ml) was added solution of Step A product (1.2 g, 3.9 mmol) in THF (30 mL) at 0C, the reaction mixture was allowed to warm to room temperature and stirred for 3 hours. When TLC showed that the reaction completed, the reaction mixture was quenched with sat. aq. NH4C1 (50 mL) and the mixture was filteredthrough a pad of celite. The filtrate was extracted with EtOAc (100 mL), washed with H20 (100 mL) and brine (100 mL), dried over Na2504 and concentrated under reduced pressure to afford mixture of (1 -((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo [d] imidazol-5-yl) methanol and (1- ((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d]imidazol-6-yl)methanol as an oil, which was used in next step without further purification. ?H NMR (CDC13, 400 MHz) oe 8.03 (s, 1H), 8.02(s, 1H), 7.86-7.79 (m, 2H), 7.64 (s, 1H), 7.61-7.55 (m, 1H), 7.43 (d, J= 7.3 Hz, 1H), 7.36 (d, J=8.4 Hz, 1H), 5.59 (s, 4H), 4.90 (s, 2H), 4.87 (s, 2H), 3.59-3.53 (m, 4H), 0.99-0.91 (m, 4H), 0.00 (s, 9H).To a solution of Step B product (0.3 g, 1.1 mmol) in DCM(10 ml) was added SOC12 (0.8 ml, 10.8 mmol) dropwise at 0C, then the reaction mixture was stirred at room temperature for 3 hours. When TLC showed that the reaction completed, the reaction mixture was diluted with DCM (50 mL), washed with sat. aq. NaHCO3 (50 mL) and brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure to afford a mixture of 5-(chloromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d] imidazole and 6-(chloromethyl)- 1 -((2- (trimethylsilyl) ethoxy)methyl)-1H-benzo[d]imidazole as an oil, which was used in next step without further purification. LC/MS (m/z): 297 (M+H).To a solution of Intermediate 2 (0.20 g, 0.65 mmol), Step C product (0.29 g, 0.97 mmol) in acetone (4 ml) and DMF (2 ml) was added K2C03(0.27 g, 1.9 mmol). The reaction mixture was then heated to 60 C and stirred for 6 hours. When LCMS showed that the reaction completed, the reaction mixture was diluted with EtOAc (1 OOmL), washed with H20 (100 mL)and brine (100 mL), dried over Na2504 and concentrated under reduced pressure to afford crude product as an oil, which was purified by column chromatography on silica gel (eluted with Petroleum ether/EtOAc = 1:1) to afford a mixture of tert-butyl 2-(4-hydroxy-2-oxo-1-((1-((2- (trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d]imidazol-5 -yl)methyl)- 1,2,5 ,7-tetrahydrofuro [3,4- b]pyridine -3 -carboxamido)acetate and tert-butyl 2-(4-hydroxy-2-oxo- 1 -((1 -((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d]imidazol-6-yl) methyl)- 1,2,5,7- tetrahydrofuro [3,4- b]pyridine-3-carboxamido)acetate as a solid. LC/MS (m/z): 571 (M+H).

According to the analysis of related databases, 26663-77-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; CAI, Jiaqiang; CRESPO, Alejandro; DU, Xiaoxing; DUBOIS, Byron Gabriel; LIU, Ping; LIU, Rongqiang; QUAN, Weiguo; SINZ, Christopher; WANG, Liping; (61 pag.)WO2016/49100; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem