Tag: M.W=100-200

Synthetic Route of 4857-06-1,Some common heterocyclic compound, 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, molecular formula is C7H5ClN2, 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.

[0700] 2-chloro-1H-benzo[d]imidazole (5 g, 32.8 mmol) was added to a solution of NAH (1.31 g, 32.8 mmol, 60%) in DMF(50 ml) below 10 C. After addition, the reaction mixture was stirred at 20 C for 2h. Then sem-c1 (5.46 g, 32.8 mmol,) was added to the reaction mixture. The reaction mixture was stirred at 20 C for 16hrs. Water (150 ml) and EtOAc (150 ml) were added. The organic layer was separated and washed by brine (100 ml), concentrated to give a residue. The crude product was purified by silica gel column (petroleum ether: ethyl acetate = 20: 1~ 4: 1) to give compound 264a (3.50 g, yield: 37.8%) as an oil. 1H NMR (400mhz, CDCl3) delta 7.78 – 7.71 (m, 1h), 7.54 – 7.48 (m, 1h), 7.41 – 7.32 (m, 2h), 5.62 (s, 2h), 3.66 -3.59 (m, 2h), 0.99 – 0.93 (m, 2h), 0.07 (d, j = 2.0 hz, 2h), 0.00 (s, 9h).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-1H-benzo[d]imidazole, its application will become more common.

Reference:
Patent; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; ADLER, Marc; EMAYAN, Kumaraswamy; MA, Jingyuang; (687 pag.)WO2018/64119; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 4857-06-1, 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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

2-chloro- 1 -methyl- 1 H-benzo [d] imidazole[670] To a solution of 2-chloro- lH-benzo[d]imidazole (2.0 g, 13.1 mmol) in DMF(10 mL) was added NaH (0.63 g, 15.7 mmol) at 0 C under N2. After stirring for 30 min at 0 C, iodomethane (5.58 g, 39.3 mmol) was added and the mixture was stirred at room temperature for additional 1 hour. The reaction mixture was quenched with water (100 mL). The aqueous layer was extracted with EtOAc (3 x 20 mL). The combined organic layers were dried over a2S04, filtered, and concentrated to give the title compound (1.9 mg, 8.9 mmol, 67.9 % yield) as a white solid. MS: MS (M+H)+; XH NMR (400 MHz, CDC13): ? 7.71-7.68 (m, 1H), 7.31-7.27 (m, 3H), 3.79 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-1H-benzo[d]imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ABBVIE INC.; BAYBURT, Erol K.; CLAPHAM, Bruce; COX, Phil B.; DAANEN, Jerome F.; GOMTSYAN, Arthur; KORT, Michael E.; KYM, Philip R.; VOIGHT, Eric A.; SCHMIDT, Robert G.; DART, Michael J.; GFESSER, Gregory; WO2013/62966; (2013); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 36947-68-9, A common heterocyclic compound, 36947-68-9, name is 2-Isopropyl-1H-imidazole, molecular formula is C6H10N2, 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.

Reference Example 110: 2-Methyl-2-(3-nitro-phenyl)-propionic acid 2-(2- isopropyl-imidazol-l-yl)-ethyl esterTo a solution of 2-methyl-2-(3-nitro-phenyl)-propionic acid 2-bromo-ethyl ester (1.5_g, 4.74 mmol) in DMF (8 mL) was added sodium iodide (0.73 g, 4.87 mmol) and heated at 100 C for 1 h. 2-Isopropyl-imidazole (2.15 g, 19.5 mmol) and triethylamine (2 mL, 14.6 mmol) were added and then refluxed for 4 h. The reaction was diluted with water and extracted with DCM. The organic layer was-washed thoroughly with water, dried over sodium sulfate and evaporated to obtain crude compound. Purification by column chromatography on silica gel (60-120 mesh), eluting with 30% ethyl acetate/hexane gave 2-methyl-2-(3-nitro-phenyl)-propionic acid 2-(2-isopropyl- imidazol-l-yl)-ethyl ester (320 mg, 20%) as a solid.

The synthetic route of 36947-68-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F2G LTD; WO2008/62182; (2008); A1;,
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 60-56-0 as follows. Recommanded Product: 1-Methyl-1H-imidazole-2(3H)-thione

General procedure: To a solution containing a thione (1, 6, 8, or 10, 1.0 equiv) in water (2.5 mL) and acetonitrile(1.5 mL) was added saturated aqueous ammonium hydroxide. After the solution was stirred atroom temperature for 30 min, a 3-(chloromethyl)coumarin (2, 1.5 equiv) was added and stirring wascontinued at room temperature for 15 min to 2.0 h. Acetonitrile therein was removed under reducedpressure and water was further removed under reduced pressure over P2O5 with a Kuegelrohr GKR-51apparatus (BUCHI, Flawil, Switzerland). The residue was purified by use of column chromatographypacked with silica gel to give the desired products with purity of >98.0%, as determined by HPLC(see Supplementary Materials).

According to the analysis of related databases, 60-56-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tsay, Shwu-Chen; Lin, Shu-Yu; Huang, Wen-Chieh; Hsu, Ming-Hua; Hwang, Kuo Chu; Lin, Chun-Cheng; Horng, Jia-Cherng; Chen, I-Chia; Hwu, Jih Ru; Shieh, Fa-Kuen; Leyssen, Pieter; Neyts, Johan; Molecules; vol. 21; 2; (2016);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 75370-65-9, 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. 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one, This compound has unique chemical properties. The synthetic route is as follows.

Amine 2af (1 g, 5.5 mmol) was dissolved in 20 ml of AcOEt and at 0C triphosgene (1.63 g, l equiv.) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 10ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound la (820 mg, 5.5 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 550mg of a white solid. Yield = 28% ‘HNMR (DMSO, 200 MHz) delta 2.64 (6H, s), 4.34 (2H, d, J = 5.8 Hz), 6.62 (1H, dd, J = 7.2 Hz, J’ = 1 Hz), 6.73 (1H, t), 6.83 (1H, t, J = 7.6 Hz), 6.90 (1H, dd, J = 8.2 Hz, J’ = lHz), 7.06 (2H, m), 7.31 (1H, d, J = 8.8 Hz), 8.33 (1H, bs), 9.98 (1H, bs), 10.59 (1H, bs); [M+1] 360.7 (C17H18ClN5O2 requires 359.81).

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

Reference:
Patent; PHARMESTE S.R.L.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 32673-41-9, name is 4-Imidazolemethanol hydrochloride, 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 32673-41-9, HPLC of Formula: C4H7ClN2O

EXAMPLE 1 Ethyl 2-ethoxy-6-(4-(hydroxymethyl)imidazole-1-yl)-7-nitroquinoline-3-carboxylate To a solution of ethyl 2-ethoxy-6-fluoro-7-nitroquinoline-3-carboxylate (1.00 g, 3.24 mmol) in acetonitrile (10 ml) were added 4-(hydroxymethyl)imidazole hydrochloride (2.18 g, 16.2 mmol) and successively triethylamine (3 ml), and the mixture was stirred for 16 hours at 120 C. in a sealed tube under shading. After cooling, solvent was distilled off and the residue was submitted to silica gel column chromatography [dichloromethane-methanol(50:1?20:1)] under shading to obtain 583 mg of title compound as light brown powder. Yield 47%. 1H-NMR(DMSO-d6, delta): 1.35(3H,t,J=7.3 Hz), 1.42(3H,t,J=7.3 Hz), 4.38 (2H,q,J=7.3 Hz), 4.42(2H,d,J=6.8 Hz), 4.58(2H,d,J=7.3 Hz), 5.05(1H, t,J=5.4 Hz), 7.27(1H,s), 7.88(1H,s), 8.39(1H,s), 8.50(1H,s), 8.87 (1H,s).

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-Imidazolemethanol hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kyorin Pharmaceutical Co., Ltd.; US6562839; (2003); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 16042-25-4, name is 2-Imidazolecarboxylic 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 16042-25-4, Computed Properties of C4H4N2O2

Step 1: To a solution of compound 1c (1 equivalent) in dichloromethane, compound 14a (1.5 eq.) was added sequentially.HOAT (1.5 eq.), HATU (2 eq.), DIPEA (6 eq.), stirred at room temperature for 12 hours.The solvent is then sparged off and directly isolated by column chromatography to afford intermediate 14b.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Imidazolecarboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Chinese Academy Of Sciences Shanghai Life Sciences Institute; Zhang Ao; Gao Daming; Ni Jiabin; Hu Hongli; Ding Chunyong; (55 pag.)CN107814792; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 68282-53-1,Some common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, 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 42 (Z)-1,3-Dihydro4-fluoro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-5-nitro-2H-indol-2-one (OO) STR68 To a solution of 1,3-dihydro4-fluoro-5-nitro-2H-indol-2-one (1 g, 5 mmol) in MeOH (10 mL) (Starting Material 10), was successively added, at r.t., 4-methyl-5-imidazolecarboxaldehyde (612 mg, 5.5 mmol) (Aldrich) and tetrabutyl ammonium hydroxide (11 mL, 1.0 M solution in MeOH)(Aldrich). The mixture was stirred at r.t. for 4 h. The resulting greenish precipitate was collected by suction filtration, washed with ether and air dried to yield (Z)-1,3-dihydro-4-fluoro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-5-nitro-2H-indol-2-one as a green powder. (Yield 1.14 g, 79%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methyl-1H-imidazole-4-carbaldehyde, its application will become more common.

Reference:
Patent; Hoffmann-La Roche Inc.; US6153634; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-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 3012-80-4, Product Details of 3012-80-4

General procedure: The equimolar aldehyde 3a?3d (1 mmol) and substituted phenylhydrazine 5a?5s (1 mmol) weremixed in CH3OH (10 mL) and stirred at room temperature [18]. After about 2 h, the reaction wascompleted (monitored by TLC). The residual crude was purified via silica gel column chromatogramusing a gradient mixture of petroleum ether and ethyl acetate to obtain the pure target compounds6a?6ai (in 45?80percent yield).

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

Reference:
Article; Wang, Xing; Chen, Yong-Fei; Yan, Wei; Cao, Ling-Ling; Ye, Yong-Hao; Molecules; vol. 21; 11; (2016);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 6160-65-2, 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 6160-65-2 as follows.

At 0C, a solution of 1,1′-thiocarbonyldiimidazole (206 mg, 1.10 mmol) in DCM (3 mL) was added dropwise 4-(3-aminophenyl)piperidine-1-carboxylic acid tert-butyl ester (160 mg, 0.58 mmol) in DCM (2 mL) and the mixture was stirred at room temperature for 3 hours. The reaction mixture was cooled again to 0C and a solution of ammonia in MeOH 7N (2 mL) was added dropwise. The reaction mixture was stirred at room temperature for 16 hours. Water was added and extracted with DCM. Purification by flash chromatography (silica gel, gradient to hexanes to 50% acetone). The desired product was obtained as a white foam (180 mg, 93% yield).

According to the analysis of related databases, 6160-65-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LABORATORIOS DEL DR. ESTEVE, S. A.; CUEVAS CORDOBES, FELIX; ALMANSA ROSALES, CARMEN; GARCIA LOPEZ, MONICA; (299 pag.)TW2016/27300; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem