Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 95470-42-1, name is Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate, 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 95470-42-1, Recommanded Product: Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate

(2) Ethyl 2-bromo-4-methyl-i H-imidazole-5-carboxylate (5lene (4.56 g, 25.8 nmol) were added thereto, and the mixmre g, 21.45 mmol) was dissolved in DMF (40 mE), potassium carbonate (5.93 g, 42.9 mmol) and 1 -(chloromethyl)naphthaNwas stirred at 80¡ã C. for 2 hours. After the reaction, water wasThe organic layer was washed with samrated aqueous sodiumadded and the mixture was extracted twice with ethyl acetate.chloride and dried over anhydrous sodium sulfate. Afier con-centrating the organic layer, the residue was purified by column chromatography to obtain ethyl 2-bromo-4-methyl-1 – (naphthalen-1 -ylmethyl)-i H-imidazole-5-carboxylate (3.2510129] ?H-NMR (CDC13) oe: 8.01 (1H, d, J=8.3 Hz), 7.91(1H, d, J=7.8 Hz), 7.77 (1H, d, J 8.3 Hz), 7.63-7.53 (2H, m),7.33 (1H, t, J=7.6 Hz), 6.43 (1H, dd, J=7.3, 1.0Hz), 6.07 (2H,s), 4.13 (2H, q, J=7.i Hz), 2.58 (3H, s), 1.11 (3H, t, J=7.i Hz);10130] ESI-MS mlz=373 (M+H).

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Reference:
Patent; Teijin Pharma Limited; Maruyama, Akinobu; Kamada, Hirofumi; Fujinuma, Mika; Takeuchi, Susumu; Saitoh, Hiroshi; Takahashi, Yoshimasa; US2015/284358; (2015); 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. 73746-45-9, name is 5-Iodo-2-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Iodo-2-methyl-1H-imidazole

PREPARATION 73 1-(3-Methyl-4-nitrophenyl)-4-iodo-2-methylimidazole, m.p. 146-148, was prepared similarly to Preparation 20 using using 4-fluoro-2-methylnitrobenzene, 4-iodo-2-methylimidazole and sodium carbonate as the starting materials with dimethylformamide as the solvent. Analysis %: Found: C, 38.5; H, 3.1; N, 12.4; Calculated for C11 H10 N3 O2 I: C, 38.5; H, 2.9; N, 12.2;

The synthetic route of 73746-45-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US4728653; (1988); A;,
Imidazole – Wikipedia,
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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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

To 400 mL of N-methyl-2-pyrrolidone, 80.0 g (261 mmol) of compound [1] and 0.43 g (5.2 mmol) of cyclohexene were added, and 43.5 g (366 mmol) of thionyl chloride was added dropwise at 20 to 40 C., followed by 60 C. The temperature was raised and the reaction was carried out for 1 hour. After confirming the reaction end point, a solution prepared by dissolving 63.0 g (261 mmol) of compound [3] in 400 mL of N-methyl-2-pyrrolidone was added dropwise to the reaction mass, and the mixture was reacted at 60 C. for 3 hours. After 400 mL of water was introduced into the reaction mass, the temperature was raised to 80 C, 83.0 g of a 20% KOH aqueous solution was added dropwise, and the temperature was kept at 80 C for 3 hours or more.Subsequently, 112.3 g of a 20% KOH aqueous solution was added dropwise over 1 h. After cooling to 60 C., 45.2 g of a 40% K 2 CO 3 aqueous solution was added dropwise, and the mixture was cooled to 40 C. over about 2 hours. The obtained crystals were dried under reduced pressure to obtain 128.6 g of compound [4] (nilotinib) (yield 93.0%). The area percentage of the peak of the target substance in the LC chromatogram was 99.96% (nuclear chlorinated product was not detected).

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; Sumitomo Chemical Co., Ltd.; Kumazawa, Hiroharu; Akiyama, Masaki; (8 pag.)JP2020/7240; (2020); A;,
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Adding a certain compound to certain chemical reactions, such as: 87233-54-3, name is 2-Chloro-1-(2-ethoxyethyl)-1H-benzo[d]imidazole, 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 87233-54-3, Quality Control of 2-Chloro-1-(2-ethoxyethyl)-1H-benzo[d]imidazole

Combine 2-chloro-1-(2-ethoxyethyl)-1H-benzimidazole (22.3 g, 99.4 mmol), 1-methyl[1,4]diazepane (19 mL, 152.8 mmol), and triethylamine (75 mL). Heat to 70 C. After 18 hours, add 1-methyl[1,4]diazepane (10 mL) and continue to heat at reflux. After 96 hours, cool to ambient temperature and partition the reaction mixture between water and ethyl acetate. Separate the layers and extract the organic layer with a saturated aqueous sodium bicarbonate solution and then brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluding sequentially with 50% ethyl acetate/hexane and then 10% methanol/dichloromethane to give 1-methyl-4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane: Rf=0.52 (silica gel, dichloromethane/methanol/concentrated aqueous ammonia, 90/10/0.1).

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Reference:
Patent; Aventis Pharmaceuticals Inc.; US6194406; (2001); B1;,
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. 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate

Example 45: Synthesis of 4-(4-Methyl-[l,4]diazepan-l-yl)-l,7,llb-triaza-benzo[c]fluorene- 6-carboxylic acid ethyl ester (Compound 8A) [0329] To a solution of SMI (176 mg, 1 mmol) and SM2 (204 mg, 1 mmol) in 2- Methoxyethanol (10 mL) was added N-Methylhomopiperazine (342 mg, 3 mmol) and the mixture was stirred at room temperature for 20 min. The reaction mixture was heated to reflux for 16h. The crude product was purification by gel silica column (DCM/MeOH=50: l) to get compound 8A as brown oil (320 mg, 79 yield). LCMS: m/z 404 (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:
Patent; HADDACH, Mustapha; WO2015/172123; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 13275-42-8, name is 2-(2-Bromophenyl)-1H-benzo[d]imidazole, 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 13275-42-8, category: imidazoles-derivatives

General procedure: Equimolar quantity of 2-(2-bromophenyl)-1H-benzo[d] imidazole (2) and aniline derivatives in 45 ml of 1,4-dioxan was refluxed for 14 hr with continuous stirring at 80. The completion of reaction was checked by TLC. The reaction mixture was kept overnight in a refrigerator. The solvent was evaporated and a gummy solid mass was obtained. The gummy solid was then washed with cold water and recrystallized from ethanol and water (4:6) to obtain the compounds (3a-3h).

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Reference:
Article; Singh, Aruna Chandra; Mittal, Nitin; Pathak, Devender; Indian Journal of Heterocyclic Chemistry; vol. 23; 3; (2014); p. 225 – 232;,
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Imidazole | C3H4N2 – PubChem

Application of 1231930-33-8,Some common heterocyclic compound, 1231930-33-8, name is 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole, molecular formula is C11H12BrFN2, 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 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo [d] imidazole (9.0 g, 33.2 mmol)Bis-boronic acid pinacol ester(0.65 g, 49.8 mmo1), palladium acetate (840 mg), tricyclohexylphosphine (1.63 g) and potassium acetate (9,78 g, 99.8 mmo 1) were added to 60 mL of DMSO and the nitrogen was allowed to warm to 80 C for 6 h.The organic phase was extracted with EA, and the organic phase was washed with EA. The organic phase was dried with anhydrous sodium sulfate and filtered through the filtrate. The filtrate was concentrated and purified by silica gel column chromatography (PE: EpsilonAlpha = 1: 2) The title compound (6.0 g, yield 56.8%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole, its application will become more common.

Reference:
Patent; Shandong Xuanzhu Pharmaceutical Technology Co., Ltd.; Wu, Yongqian; (45 pag.)CN104910137; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, 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. name: 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

3-Iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)Benzamide: 3-Iodo-4-methylbenzoic acid (2.62 g, 10 mmol) was refluxed in soc2 (10 mL) for 5 1 h. The volatile components were removed on a rotavap and the residue was dissolved inbenzene (10 mL), concentrated to dryness on a rotavap and further dried under vacuum. The resulting acyl chloride was added to a solution 3-(4-methyl-IH-imidazol-I-yl)-5- (trifluoromethyl)benzenearnine (2.46 g, 10.2 mmol), N,N-diisopropylethylamine (1.56 g, 12 mmol), and a catalytic amount of DMAP in THF (20 mL). After stirring at rt for 2 h, the reaction10 was quenched with water. EtOAc was added and the layers separated. The combined organic layers were concentrated to dryness and used without purification in next step.

The synthetic route of 641571-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; GOZGIT, Joseph, M.; RIVERA, Victor, M.; SHAKESPEARE, William, C.; ZHU, Xiaotian; DALGARNO, David, C.; WO2013/162727; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 870837-70-0, name is 4-(1H-Imidazol-1-yl)-3-methoxybenzaldehyde, molecular formula is C11H10N2O2, 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. Quality Control of 4-(1H-Imidazol-1-yl)-3-methoxybenzaldehyde

Dimethylphosphonoacetic acid methyl ester (3.80 mL) and lithium hydroxide monohydrate (1.20 g) were added one by one to a THF (20 mL) solution of the crude aldehyde compound (4.76 g) obtained above, and the reaction solution was agitated overnight at the room temperature. 2N sodium hydroxide solution was added to the reaction solution after confirming disappearance of the starting materials (20 mL), and the reaction solution was agitated at 50 C. for 2 hours. The reaction solution was cooled to 0 C., 2N hydrochloric acid was added to the reaction solution (20 mL), and deposited precipitation was separated by filtering with Kiriyama funnel. The obtained precipitation was washed with water and ethyl acetate, and 4.2 g of the title compound was obtained. The physical properties of the compound are as follows. 1H-NMR (DMSO-d6) delta (ppm): 7.96 (s, 1H), 7.63 (d, J=16 Hz, 1H), 7.60 (d, J=1.6 Hz, 1H), 7.48 (s, 1H), 7.45 (d, J=8.0 Hz, 1H), 7.39 (dd, J=1.6, 8.0 Hz, 1H), 7.06 (s, 1H), 6.68 (d, J=16 Hz, 1H), 3.90 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 870837-70-0, its application will become more common.

Reference:
Patent; Eisai Co., Ltd.; US2006/4013; (2006); 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. 67085-11-4, name is 4-(4-Chlorophenyl)-1-(1H-imidazol-1-yl)butan-2-ol, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

PREPARATION 5 1-[2-Hydroxy-4-(4-chlorophenyl)-n-butyl]imidazole (2.0 g) in thionyl chloride (10 ml) is warmed for one hour at 65. The excess thionyl chloride is removed in vacuo, the residue dissolved in dichloromethane (75 ml) and shaken with excess aqueous potassium carbonate. The organic layer is washed with water, dried over MgSO4, evaporated and the residue evacuated to remove all traces of dichloromethane, affording 1-[2-chloro-4-(4-chlorophenyl)-n-butyl]imidazole.

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; Syntex (U.S.A.) Inc.; US4272545; (1981); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem