Tag: M.W=100-200

Synthetic Route of 68282-47-3, The chemical industry reduces the impact on the environment during synthesis 68282-47-3, name is 2-Phenyl-1H-imidazole-4-carbaldehyde, I believe this compound will play a more active role in future production and life.

COMPOUND 12.1. 11: NqN-DIETHYL-4- {7-METHOXY-2-[(2-PHENYL-1H- IMIDAZOL-5-YL) METHYL1-L24-TETRAHYDROISOOUINOLIN-1- YUBENZAMIDE; INTERMEDIATE 4.2. 2 (24 mg, 0.07 mmol) and 2-phenylimidazole-4 (5)- carbaldehyde (48 mg, 0.28 mmol) were dissolved in DCE (2.0 mL) and NMP (0.2 mL). After stirring for 10 min at room temperature, sodium triacetoxyborohydride (59 mg, 0.28 mmol) was added and the mixture was stirred for 18 h at room temperature. DCM and 1 M sodium hydroxide solution were added and the mixture was passed through a Whatman IPS silicon-treated filter paper. The organic phase was evaporated and the crude product was purified by flash chromatography to yield the product (13 mg, 0.026 mmol, 37%). lH NMR (500 MHz, CDC13) : 8 1. 10, 1.24 (2 brs, 6H), 2.73, 2. 82, 3. 00, 3.17 (4 m, 4H), 3.25, 3.54 (2 brs, 4H), 3.62 (s, 3H), 3.68 (m, 2H), 4.89 (s, 1H), 6.21 (s, 1H), 6.73 (d, J 8. 5 Hz, 1H), 6.90 (s, 1H), 7.05 (d, J 8. 5 Hz, 1H), 7.27-7. 38 (m, 7H), 7.90 (m, 2H). 13C NMR (125 MHz, CDC13): 6 12.8, 14.2, 26.4, 39.5, 43.4, 46.6, 49.1, 55.2, 66.9, 113.2, 113.8, 125.9, 126.5, 129.0, 129.7, 129.9, 157.9, 171.1. (+) LRESIMS m/z 495 [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, 2-Phenyl-1H-imidazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); 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. 1848-84-6, name is 2-Ethyl-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Ethyl-1H-benzo[d]imidazole

A mixture of (5-chloro-7-morpholin-4-ylthiazolo[5,4-J]pyrimidin-2-yl)-[4-(l- hydroxy-l-methylethyl)piperidin-l-yl]methanone (250 mg, 0.59 mmol), 2- ethylbenzimidazole (90 mg, 0.62 mmol), tris(dibenzylideneacetone)dipalladium (15 mg, 2.5 molpercent), XPhos (25 mg, 10 molpercent) and Cs2CO3 (270 mg, 0.83 mmol) in DMF (6 mL) was purged with argon then heated at 150 0C for 30 min in a microwave reactor. The reaction mixture was purified by column chromatography (Si-PCC, MeOH:DCM, 1-5percent) followed by recrystallisation from Et2O and EtOAc affording 771 (109 mg, 35percent). LCMS (method I): Rx 3.96 min [M+H]+ 536.3. 1H NMR (CDCl3, 400 MHz): delta 8.06-8.05 (1 H, m), 7.76-7.75 (1 H, m), 7.32-7.28 (2 H, m), 5.22 (1 H, d, J = 13.34 Hz), 4.84 (1 H, d, J = 13.16 Hz), 4.41 (4 H, brd s), 3.89 (4 H, t, J = 4.74 Hz), 3.37 (2 H, q, J = 7.46 Hz), 3.17-3.15 (1 H, m), 2.84-2.82 (1 H, m), 1.94 (2 H, t, J = 13.72 Hz), 1.72-1.62 (1 H, m), 1.49-1.40 (5 H, m), 1.23 (6 H, d, J = 7.01 Hz)

The synthetic route of 1848-84-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; CASTANEDO, Georgette; CHAN, Bryan; GOLDSTEIN, David Michael; KONDRU, Rama K.; LUCAS, Matthew C.; PALMER, Wylie Solang; PRICE, Stephen; SAFINA, Brian; SAVY, Pascal Pierre Alexandre; SEWARD, Eileen Mary; SUTHERLIN, Daniel P.; SWEENEY, Zachary Kevin; WO2010/138589; (2010); A1;,
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Imidazole | C3H4N2 – PubChem

Application of 54624-57-6,Some common heterocyclic compound, 54624-57-6, name is 2-Bromobenzimidazole, molecular formula is C7H5BrN2, 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: To the corresponding benzimidazole or pyrazole 16?20 (4.5 or 6.6 equiv), dissolved under N2 atmosphere in anhyd MeCN, NaH (60percent dispersion in mineral oil, 4.5 or 6.6 equiv) was added and the mixture was stirred for 30 min at r.t. Then, the bromomethyl-substituted benzene derivative 15, 21 or 23 (1 equiv) was added and the reaction mixture was stirred for up to 5 d at r.t. under N2 atmosphere. The reaction was quenched with H2O (10 mL) and extracted with CHCl3 (3 × 10 mL). The organic layers were combined, dried over MgSO4 and filtered, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography using CHCl3?MeOH or CHCl3?MeOH?hexane as the eluent.

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

Reference:
Article; Koch, Niklas; Mazik, Monika; Synthesis; vol. 45; 24; (2013); p. 3341 – 3348;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 33543-78-1, The chemical industry reduces the impact on the environment during synthesis 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, I believe this compound will play a more active role in future production and life.

Example 3A Ethyl 1-[2-(2,4-dichlorophenyl)-2-oxoethyl]-1H-imidazole-2-carboxylate 0.5 g (3.6 mmol) of imidazole-2-carboxylate ethyl were dissolved in 35 ml of acetone, and 0.96 g (3.6 mmol) of 2-bromo-2,4-dichloroacetophenone and 0.49 g (3.6 mmol) of potassium carbonate were added. The mixture was stirred at RT for 12 h. The reaction mixture was concentrated and taken up in water and dichloromethane. The organic phase was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated on a rotary evaporator. The residue was triturated with diethyl ether and the solid was filtered off with suction. This gave 0.9 g (77percent of theory) of the product as a solid. LCMS (method 1): Rt=1.19 min. (m/z=327 (M+H)+) 1H-NMR (400 MHz, DMSO-d6): delta=7.96 (d, 1H), 7.84 (d, 1H), 7.68 (dd, 1H), 7.5 (s, 1H), 7.16 (s, 1H), 5.87 (s, 2H), 4.22 (q, 2H), 3.32 (s, 2H), 1.23 (t, 3H).

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, Ethyl 1H-imidazole-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2011/53929; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 75370-65-9, 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. 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 3 1-(2-chloro-4-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-4-yl)urea (scheme 1) Commercially available 2-chloro-4-trifluoromethylbenzylamine (700 mg, 3.3 mmol) was dissolved in 20ml of AcOEt and at 0C triphosgene (989mg, 3.3mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (5 ml) of compound 1a (319 mg, 2.14 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 9.5 / MeOH 0.5). The solvent was evaporated and the crude was dissolved in AcOEt (30ml) 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 140 mg of a white solid. Yield = 18% 1HNMR (DMSO, 400 MHz) delta 4.44 (2H, d, J = 5.6 Hz), 6.64 (1H, d, J = 7.2 Hz), 6.84 (1H, t, J = 8.4 Hz), 6.89 (1H, t), 6.96 (1H, d, J = 8 Hz), 7.64 (1H, d, J = 8.4 Hz), 7.74 (1H, d), 7.86 (1H, s), 8.43 (1H, bs), 9.99 (1H, bs), 10.61 (1H, bs); [M+1] 385.0 (C16H12C12C1F3N4O2 requires 384.74).

The synthetic route of 4-Amino-1H-benzo[d]imidazol-2(3H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pharmeste S.r.l.; EP2377850; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 17325-26-7, 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 17325-26-7 as follows.

Into an 18 mL vial was added Methyl 4-imidazolecarboxylate (113 mg, 0.90 mmol), DMF (3 mL), and NaH (43 mg, 1.08 mmol). After 20 minutes at room temperature Int-20 (295 mg, 0.90 mmol) was added. The reaction was stirred for 2 hours at room temperature and then water was added. The product was extracted with EtOAc and the organics were concentrated. The residue was purified by flash column chromatography eluting with 6%-10% Acetone/DCM to separate the regioisomers. The 4-substituted ester (Int-53, 67 mg, 20%) and the 2-substituted ester (Int-54, 79 mg, 23%) were obtained as colorless oils.

According to the analysis of related databases, 17325-26-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DECODE GENETICS EHF; US2009/136473; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 29043-48-9, These common heterocyclic compound, 29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, 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 coupling reaction of 3-chloro-2-methylbenzenesulphonyl chloride (2 eq. ) with 2- methylbenzimidazoel (1 eq. ) under the condition described above yielded a mixture of 3- CHLORO-N- [1- (3-CHLORO-2-METHYLBENZENESULPHONYL)-2-METHYL-1 H-BENZOIMIDAZOL-5-YL]-2- methyl-benzenesulphonamide and 3-chloro-N-[1-(3-chloro-2-methylbenzenesulphonyl)- 2-METHYL-1 H-BENZOIMIDAZOL-6-YL]-2-METHYL-BENZENESULPHONAMIDE in 1: 1 ratio as judged by HNMR.’H NMR (270 MHz, DMSO): 5 10.7 (2H, s, 2 x NH), 7.86-7. 96 (3H, m, ArH), 7.65-7. 78 (5H, m, ArH), 7.52-7. 58 (5H, m, ArH), 7.25-7. 40 (3H, m, ArH), 7.07 (2H, t, J = 8.2 Hz, ArH), 2.61 (3H, s, CH3), 2.58 (3H, s, CH3), 2.54 (6H, s, 2 x CH3), 2.39 (3H, S, CH3), 2.33 (3H, s, CH3). The mixture (200 mg) was dissolved in THF (15 mL), N- hydroxybenzotriazole (200 mg) was added. After stirred at rt for 48h, the mixture was partitioned between ethyl acetate and 5% sodium bicarbonate. The organic phase was washed with brine, dried over sodium sulphate and concentrate in vacuo to give a yellow residue, which was purified with flash chromatography (methanol/DCM gradient elution). Off white amorphous powder was obtained. TLC single spot at Rf 0.38 (10% methanol/DCM) ; HPLC purity 99% (tR 2.0 min in 10% WATER-METHANOL) ;’H NMR (270 MHz, DMSO): 5 12.1 (1H, s, NH), 10.3 (1H, s, NH), 7.78 (1H, d, J = 7.9 Hz, ArH), 7.68 (1H, d, J= 7.9 Hz, ArH), 7.29-7. 35 (2H, m, ArH), 7.12 (1H, s, ArH), 6.83 (1H, dd, J= 8.4, 1.8 Hz, ArH), 2.63 (3H, s, CH3), 2.41 (3H, s, CH3) ; APCI-MS 334 (M-H+) ; FAB-HRMS calcd for C1SH1SCIN302S (MH+) 336.0573, found 336.0583.

Statistics shows that 2-Methyl-1H-benzoimidazol-5-ylamine is playing an increasingly important role. we look forward to future research findings about 29043-48-9.

Reference:
Patent; STERIX LIMITED; WO2004/37251; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 2034-23-3, 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 2034-23-3 as follows.

Example 27; Prcparatiort of 5-((butyIthio)acetyl)-6-chloro-l,3-dimethyl-l,3-dihydro-2f/- benzimidazol-2-one (27); (i) 5-Chl«?>- ,3-dime-liyl-l,3-dihydr-2H-beimaiidazo.-2-onc; 5-Chloro-l ,3-dihydro-2/?-ben^imidazol-2-0Qc (7.040 g, 41.8 mmol) was dissolved in anhydrous DMF (100 ml), anhydrous potassium carbonate (34.707 g, 251 mmol) and iodomcthane (15.5 ml, 249 mmol) were added and the mixture stirred at room temperature overnight. The reaction mixture was poured into chloroform (400 ml) and mixed well then filtered and the filtrate evaporated to dryness. The resultant residue was dissolved in a mixture of ethyl acetate (500 in I) and water (200 ml), the ethyl acetate phase was washed with water (2 x 100 ml) and brine (100 ml), dried over anhydrous magnesium sulfate and filtered, The filtrate was evaporated to dryness to give the title compound (J.163 g, 87% yield) as a brown powder.1H nmr (400 MH?-, CDCIa) delta 3.37-3.42 (m, 6H); 6.87 (d, J – 8.0Hz, IH); 6.97 (d, J = 1.6Hz, IJ I); 7.07 (dd, J = 8.2, 1.8Hz, IH).

According to the analysis of related databases, 2034-23-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CORTICAL PTY LTD; WO2007/70961; (2007); 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. 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, A new synthetic method of this compound is introduced below., SDS of cas: 39070-14-9

A solution of triphosgene (62 mg, 0.21 mmol) in DCM (4.0 mL) was added to a stirred solution of A13 (prepared as described in: WO 2013/055987; 500 mg, 0.52 mmol) and Et3N (120 mg, 1.18 mmol) in DCM (20 mL) at 22 C. The mixture was stirred at that temperature for 2 h. A solution of (1-methyl-2-nitro-1H-imidazol-5-yl)methanol (112 mg, 0.71 mmol) in DCM (1 mL) was then added, followed by nBu2Sn(OAc)2 (3 drops). The resulting solution was stirred at 22 C for 16 h under N2 then was concentrated under reduced pressure. The residue was purified by prep-TLC (DCM/MeOH = 30/1) to give A14 as a yellow solid (180 mg, 31%). LCMS (condition A): RT = 1.11 min, m/z = 1136.9 [M+H]+.

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; Dragovich, Peter S.; Broccatelli, Fabio; Chen, Jinhua; Fan, Peter; Le, Hoa; Mao, Weiguang; Pillow, Thomas H.; Polson, Andrew G.; Wai, John; Xu, Zijin; Yao, Hui; Zhang, Donglu; Bioorganic and Medicinal Chemistry Letters; vol. 27; 23; (2017); p. 5300 – 5304;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 39021-62-0, A common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, molecular formula is C5H6N2O, 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.

General procedure: A solution (0.05mol-%) of the appropriate furan-2-one (1 eq.) in dry diethyl ether (DEE) was mixed with the N-heterocyclic carbaldehyde (1, 2 or 3 eq.) under a nitrogen atmosphere at 0C. After stirring for 30min, excess dry diethylamine (4 eq.) was added dropwise. Stirring was continued for 30min. The solution was allowed to warm up over night and the product usually precipitated as fluffy powder. The precipitate was washed with cold DEE and dried in vacuo.

The synthetic route of 39021-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Uhrner, Fabian; Lederle, Felix; Namyslo, Jan C.; Gjikaj, Mimoza; Schmidt, Andreas; Huebner, Eike G.; Tetrahedron; vol. 73; 30; (2017); p. 4472 – 4480;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem