Tag: M.W=100-200

Reference of 29518-68-1,Some common heterocyclic compound, 29518-68-1, name is 2-(1H-Benzo[d]imidazol-2-yl)ethanamine, molecular formula is C9H11N3, 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.

Under argon protection, [RuCl2(C6H6)] 28.2 mg (0.0164 mmol) and (S)-SEGPHOS 20 mg (0.0328 mmol) was suspended in 2 ml of argon gas degassed DMF.Stir at 100 C for 1 hour; The solvent was removed under vacuum at 50 C. Obtained a brown solid; Then, add beta-bimaH 5.3 mg (0.0328 mmol) and2.6 ml of argon gas degassed DCM (dichloromethane)-methanol mixed solvent (DCM:methanol = 10:3),Then add Et3N9.9mg (0.0984mmol),Stir at room temperature for 12 hours under argon protection; The solvent was removed in vacuo, 3 mL DCM was added and filtered.The filtrate was concentrated under reduced pressure to about 0.5 ml.Add 3 ml of n-hexane to precipitate, filter, wash twice with 3 mL of diethyl ether, and dry in vacuo.The product was obtained in 23.3 mg (yield 76%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(1H-Benzo[d]imidazol-2-yl)ethanamine, its application will become more common.

Reference:
Patent; Zhongshanyi Antai Pharmaceutical Technology Co., Ltd.; Ke Lisidian·A·shanduofu; Xu Liang; Pa Telike·boermate; A Shenli·woke; (18 pag.)CN103889995; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 89088-69-7, name is 1-Methyl-1H-imidazol-4-amine hydrochloride, 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. COA of Formula: C4H8ClN3

Intermediate 69; 6-Chloro-iV-( 1 -methyl- lH-imidazol-4-vO- 1 -(tetrahvdro-2H-pyran-2-vO- 1 H-pyrazolo [3 A- dlpyrimidin-4-amineTo a solution of 4,6-dichloro-l-(tetrahydro-2H-pyran-2-yl)-lH-pyrazolo[3,4-d]pyrimidine(Intermediate 70, 3.168 g, 11.60 mmol) in ethanol (60 mL), was added TEA (4.04 mL, 29.00 mmol) followed by 1 -methyl- lH-imidazol-4-amine hydrochloride (Intermediate 36, 1.549 g,11.60 mmol). The resulting mixture was heated at 600C for 2 hours. Evaporation of the volatiles under reduced pressure gave a residue, which was purified utilizing ISCO (EtOAc/hexanes0->80%) to give the title product (1.56g).LCMS: 334 [M+Eta]+.

The synthetic route of 1-Methyl-1H-imidazol-4-amine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; CHUAQUI, Claudio, Edmundo; HUANG, Shan; IOANNIDIS, Stephanos; SHI, Jie; SU, Mei; SU, Qibin; WO2010/38060; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 149520-94-5, A common heterocyclic compound, 149520-94-5, name is Ethyl 2-amino-1H-imidazole-5-carboxylate, molecular formula is C6H9N3O2, 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.

The mixture of 2-amino-lH-imidazole-4-carboxylic acid ethyl ester (220 mg, 1.42 mmol, 1.0 eq), 3-chloro-6-chloromethyl-quinoline (301 mg, 1.42 mmol, 1.0 eq) and K2C03 ( 294 mg, 2.13 mmol, 1.5 eq) in DMF ( 8 mL) was stirred at 50 C overnight. The reaction mixture was diluted with water and extracted with EA. The combined organic layers was dried and concentrated. The resulting residue was purified by chromatography on a silica gel column (DCM/MeOH = 20/1, v/v) to give 2-amino-l-(3-chloro-quinolin-6- ylmethyl)-lH-imidazole-4-carboxylic acid ethyl ester (100 mg, 21%) and 2-amino-3-(3- chloro-quinolin-6-ylmethyl)-3H-imidazole-4-carboxylic acid ethyl ester (120 mg, 26%) as a yellow solid.

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.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (346 pag.)WO2018/11628; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 29518-68-1, name is 2-(1H-Benzo[d]imidazol-2-yl)ethanamine, A new synthetic method of this compound is introduced below., Product Details of 29518-68-1

General procedure: To a 50-ml glass round-bottom flask was added sequentially the primary amine 2 (1.0 mmol; aliphatic, aromatic or heteroaromatic; as free naked amine or as HCl, MsOH, TsOH or tartrate salt), FSO2N3 solution (containing 1.0 mmol FSO2N3, approximately 200 mM in DMF/MTBE 1:1, v/v, approximately 5 ml, volume adjusted according to the concentration; prepared according to the above procedure and diluted with equal volume of DMF) and aqueous KHCO3 solution (3.0 M, 1.33 ml, containing 4.0 mmol KHCO3). The reaction mixture was stirred for 5 min at room temperature, while monitoring by LC-MS. After completion, EtOAc (40 ml) was added and the mixture was washed sequentially with brine (60 ml × 6), water (60 ml × 2) and brine (60 ml), dried over Na2SO4, concentrated by rotary evaporation and dried under vacuum to afford the azide product 3. For products containing acidic functional groups, this extraction process was modified with acidified aqueous phase (acidified with aqueous HCl). Detailed procedures and the various modifications, as well as the characterization data for each compound, can be found in Supplementary Information 1.

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.

Reference:
Article; Meng, Genyi; Guo, Taijie; Ma, Tiancheng; Zhang, Jiong; Shen, Yucheng; Sharpless, Karl Barry; Dong, Jiajia; Nature; vol. 574; 7776; (2019); p. 86 – 89;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 26530-93-8,Some common heterocyclic compound, 26530-93-8, name is 1-Methyl-1H-benzo[d]imidazol-6-amine, molecular formula is C8H9N3, 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 No. 148Preparation of (8-Methoxy-2H-pyrazolo [3 , 4-c] quinolin-4-yl) – (3- methyl-3H-benzoimidazol-5-yl) -amine4-chloro-8-methoxy-2- (4-methoxybenzyl) -2H-pyrazolo [3,4- c]quinoline (0.16 mmol) and l-methyl-lH-benzoimidazol-6-amine (2 eq.,0.3 mmol) 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 140 °C. The reaction mixture was evaporated and used without further purification. 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: 344.1599 g/mol HPLC-MS: analytical method Brt: 1.518 min – found mass: 345.1 (m/z+H)

The synthetic route of 26530-93-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORIGENIS GMBH; ALMSTETTER, Michael; THORMANN, Michael; TREML, Andreas; KOESTLER, Roland; YEHIA, Nasser; WO2012/143143; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 253453-91-7, 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. 253453-91-7 name is 2-Chloro-1-methyl-1H-imidazole, 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.

Step C: (2-Chloro-3-methyl-3H-imidazol-4-yl)-(4-chloro-phenyl)-methanone. To a 1-L, three-necked, round-bottomed flask equipped with a magnetic stirrer, nitrogen inlet and an addition funnel was added 2-chloro-1-methyl-1H-imidazole (15 g, 0.128 mol) and THF (250 mL). The reaction mixture was cooled to -78 C. and n-BuLi (2.5 M in hexanes, 54 mL, 0.135 mol) was added. The pale yellow suspension that formed was stirred for 1 h and a solution of 4-chloro-N-methoxy-N-methyl-benzamide (27 g, 0.135 mol) in THF (50 mL) was then added dropwise. After the addition was complete, the cooling bath was removed and the reaction was allowed to warm to rt. The reaction mixture was quenched with satd. aq. NH4Cl (150 mL), transferred to a separatory funnel, and extracted with EtOAc (1.5 L). The organic layer was washed with water, brine and dried over anhydrous Na2SO4. After filtration, the solvents were evaporated under reduced pressure to yield the product as a crystalline solid. Recrystallization from EtOAc-hexanes afforded the desired ketone (31.2 g, 97%) as a white crystalline solid. mp 173-174 C. IR (film): 1639, 1589, 1517, 1395, 1377, 1253, 1186, 902, 841, 756, 738, 695, 676 cm-1. 1H NMR (400 MHz, CDCl3): delta7.78 (d, J=8.6 Hz, 2H), 7.44 (s, 1H), 7.44 (d, J=8.6 Hz, 2H), 3.97 (s, 3H). 13C NMR (100 MHz, CDCl3): delta183.3, 140.3, 139.5, 139.2, 136.3, 131.2, 130.4, 128.9, 33.5. HRMS (EI): m/z calcd for C11H9Cl2N2O [M+H]+, 255.0092; found, 255.0104. Anal. Calcd for C11H8Cl2N2O: C, 51.8; H, 3.06; N, 10.93. Found: C, 52.08; H, 3.16; N, 10.90.

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

Reference:
Patent; Jones, Todd K.; Mani, Neelakandha; US2005/250948; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 13750-81-7, 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. 13750-81-7, name is 1-Methyl-1H-imidazole-2-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 76A1 -Ethyl- lH-imidazole-2- carbaldehyde[00631] To a suspension of lH-imidazole-2- carbaldehyde (480 mg, 5 mmol) and potassium carbonate (936 mg, 6 mmol) in N, N-dimethylformamide (7 mL) was added iodoethane (829 mg, 6mmol) and the mixture was heated at 50 C for 5 hrs. Solvent was removed under reduced pressure. The residue was partitioned between water (30 mL) and ethyl acetate (30 mL). The aqueous layer was extracted with ethyl acetate (20 mLx3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give 1 -ethyl- lH-imidazole-2- carbaldehyde as light yellow oil (520 mg, yield 84%). 1H MR (400 MHz, CDC13) delta (ppm): 1.42- 1.46 (t, J= 7.2 Hz, 3H), 4.42-4.47 (q, 2H), 7.19 (s, IH), 7.29 (s, IH), 9.82 (s, IH). LC-MS (ESI) m/z: 125 (M+l)+.

The synthetic route of 1-Methyl-1H-imidazole-2-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHU, Daniel; WO2011/130661; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 857070-66-7, name is (2-Chloro-1H-benzo[d]imidazol-6-yl)methanol, A new synthetic method of this compound is introduced below., Application In Synthesis of (2-Chloro-1H-benzo[d]imidazol-6-yl)methanol

A mixture of b-3 (0.069 mol) and N-propylamino-morpholine (0.207 mol) was stirred at 125C for 4 hours, and then taken up in CH2C12/CH3OH. The organic layer was washed with a 10% solution OfK2CO3 in water, dried (over MgSO4), filtered and the solvent was evaporated until dryness. The residue (37 g) was purified by column chromatography over silica gel (eluent: CH2C12/CH3OH/NH4OH 90/10/0.5; 20-45mum). The pure fractions were collected and the solvent was evaporated, yielding 16.5g of intermediate b-4 (82%).

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.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD; WO2006/136562; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 17450-34-9, name is Ethyl 2-(1-Imidazolyl)acetate, 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. Recommanded Product: 17450-34-9

Take the above compounds Intermediate 1 is 7.7g (0.05mol) was dissolved in 100mL of water, concentrated hydrochloric acid to adjust the pH value of 1.5, refluxed for 7h at 100 deg.] C, After completion of the reaction, the resultant reaction liquid was distilled under reduced pressure at 25 deg.] C directly to the not drop out of the droplet, was added 300 mL of acetone to give a white solid was filtered and recrystallized from isopropanol to give white crystals, i.e. intermediate compound 2;

The synthetic route of Ethyl 2-(1-Imidazolyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Atomic Medical Institute; Lin Jianguo; Peng Ying; Qiu Ling; Lv Gaochao; Li Ke; Luo Shineng; Zhao Xueyu; Wang Shanshan; (22 pag.)CN106749405; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2080-75-3, name is 5-Methoxy-1H-benzo[d]imidazol-2(3H)-one, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 2080-75-3

Intermediate 38:[0169] A mixture of intermediate 37 (3.6 g, 22 mmol) and 48% hydrogen iodide (30 mL) was heated to reflux (130C) and stirred for 12 h. The reaction mixture was neutralized to pH = 8 with aq NaOH and then extracted with EtOAc. The combined organic layers were dried over anhydrous Na2S04, concentrated under vacuum and purified by flash chromatography on silica gel column (elution with DCM/MeOH = 80: 1) to give 5-hydroxy-lH-benzo[cf]imidazol-2(3H)- one (intermediate 38) (16.9 g, 80%). HPLC: 99%, RT 1.377 min. MS (ESI) m/z 151.0 [M + H]+. mp: 186-187C

The synthetic route of 2080-75-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; JIN, Jian; ROTH, Bryan; FRYE, Stephen; WO2012/3418; (2012); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem