Tag: M.W=100-200

934-22-5, A common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, molecular formula is C7H7N3, 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 1; The preparation of 3-(1H-benzimidazol-5-ylamino)-4-(3-hydroxybenzylamino)cyclobut-3-ene-1,2-dione (?A1?) is carried out analogously to the following scheme 1.1 6.2 g (35.7 mmol) of 3,4-diethoxy-3-cyclobutene-1,2-dione 1 are dissolved in 50 ml of ethanol, 5.0 g (35.7 mmol) of 3H-benzimidazol-5-ylamine 2 are added, and the mixture is stirred at 75 C. for 20 h. The mixture is then subjected to conventional work-up, giving 8.93 g (97%) of 3-(1H-benzimidazol-5-ylamino)-4-ethoxycyclobut-3-ene-1,2-dione 3; MS-FAB (M+H+)=358, m.p. 243-244.

The synthetic route of 934-22-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mederski, Werner; Emde, Ulrich; Barnickel, Gerhard; Zenke, Frank; Greiner, Hartmut; Stieber, Frank; US2008/234266; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

33468-67-6, 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. 33468-67-6 name is 2-Methyl-4-(trifluoromethyl)-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.

Compound 16.3. 2-Methyl-lH-imidazole-4-carbonitrile. Into a 100-mL round- bottom flask, was placed a solution of 2 -methyl-4-(trifluoromethyl)-lH- imidazole (compound 16.2, 300 mg, 2.00 mmol) in 5% ammonium hydroxide (35 mL). The resulting solution was stirred for 4 days at room temperature, then the pH of the solution was adjusted to 7 with acetic acid. The aqueous phase was extracted with of ethyl acetate (3 x 10 mL) and the combined organic layers were dried (Na2S04), filtered, and concentrated under reduced pressure to yield 170 mg (79%) of the title compound as a light yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Methyl-4-(trifluoromethyl)-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; 3-V BIOSCIENCES, INC.; OSLOB, Johan D.; MCDOWELL, Robert S.; JOHNSON, Russell; YANG, Hanbiao; EVANCHIK, Marc; ZAHARIA, Cristiana A.; CAI, Haiying; HU, Lily W.; WO2014/8197; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1615-14-1, Name is 2-(1H-Imidazol-1-yl)ethanol, 1615-14-1, 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.

Synthesis of benzyl (25,4a5,6a5,6bR,8a5, lOS, 12a5, l2bR, l4bR)-10-((2-(2-(1H-Imidazol-1-yl)ethoxy)-2-oxoethyl)carbamoyl)-2,4a,6a,6b,9,9, 1 2a-heptamethyl- 13 -oxo- 1,2,3 ,4,4a, 5,6,6a,6b,7, 8,8a,9, 10,11,12,1 2a, 1 2b, 13,1 4b-icosahydropicene-2-carboxylate (44-1). Into a 1 00-mL roundbottom flask, was placed EDCI (53.4 mg, 0.28 mmol, 1.50 equiv.), DCM (15 mL), DMAP (113 mg, 0.92 mmol, 5.00 equiv.). The resulting solution was stirred for 1 h at room temperature. 30- 2 (120 mg, 0.19 mmol, 1.00 equiv.) was added. The resulting solution was allowed to react, withstirring, for an additional 1 h at 55 C. 2-(1H-imidazol-1-yl)ethan-1-ol (83 mg, 0.74 mmol, 4.00 equiv.) was added. The resulting solution was allowed to react, with stirring, for an additional overnight at 55 C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with DCM/MeOH (9:1). This resulted in 85 mg (62%) of 44-1 as an off-white solid.

Statistics shows that 2-(1H-Imidazol-1-yl)ethanol is playing an increasingly important role. we look forward to future research findings about 1615-14-1.

Reference:
Patent; ARDELYX, INC.; LUEHR, Gary; DRAGOLI, Dean; LEADBETTER, Michael; CHEN, Tao; LEWIS, Jason; (181 pag.)WO2019/60051; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

872-49-1, 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. 872-49-1, name is 5-Chloro-1-methylimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5-Chloro-1-methyl-imidazole (4.0 g, 34.32 mmol) was dissolved in a mixture of 4.0 g of conc. nitric acid and 14 mL of water, and concentrated in vacuo to give a yellow slurry. To this mixture was added dropwise 12 g of conc. sulfuric acid and heated to 95C for 2 hours. Upon cooling, ice was added to the reaction mixture, which was then left standing 10 hours at 5C. The white precipitation was collected by filtration, washed with water, recrystallized from ethanol and dried in vacuo to give compound 60A.

The synthetic route of 5-Chloro-1-methylimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; EP1066286; (2009); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. 2849-93-6

General procedure: To a solution of the intermediate acid compound 1a-f (1 equiv.)in anhydrous DMF was added EDCI (1.1 equiv) and HOBt (1.1equiv), respectively. The reaction mixture was stirred for 1 h at ambient temperature, and the L-serine ester (1.1 equiv.) and DIEA(3 equiv.) were added. The solution was heated to 70 C for 6 hand then cooled to room temperature. The reaction mixture was poured into ice water, and the resulting solid was filtered and dried to give the desired compound.

The synthetic route of 2849-93-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhao, Shizhen; Wei, Peng; Wu, Mengya; Zhang, Xiangqian; Zhao, Liyu; Jiang, Xiaolin; Hao, Chenzhou; Su, Xin; Zhao, Dongmei; Cheng, Maosheng; Bioorganic and Medicinal Chemistry; vol. 26; 12; (2018); p. 3242 – 3253;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

41716-18-1, 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. 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of intermediate 42-h.HCl (1.50 g, 2.24 mmol) in DMF, cooled to 0¡ã C., were sequentially added 1-methyl-1H-imidazole-4-carboxylic acid (397 mg, 3.15 mmol), HATU (1.19 g, 3.15 mmol) and DIPEA (1.57 mL, 8.99 mmol) and the reaction mixture was stirred at room temperature for 2 hours. Saturated aqueous ammonium chloride and ethyl acetate were added; the organic layer was separated, washed with saturated aqueous ammonium chloride, saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by silica gel chromatography provided intermediate 43-a as a white foam.

The synthetic route of 41716-18-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pharmascience Inc.; Laurent, Alain; Proulx, Melanie; Rose, Yannick; Denissova, Irina; Dairi, Kenza; Jarvis, Scott; Jaquith, James B.; (189 pag.)US9284350; (2016); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2849-93-6, 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 2849-93-6 as follows.

Diisopropylethylamine (2.2 [MMOL)] was added to a solution of benzimidazole-2- carboxylic acid (3.59 [MMOL),] [0- (7-AZABENZOTRIAZOL-1-YL)-N, N, N’, N’-] [TETRAMETHYLURONIUM] hexafluorophosphate (HATU, 3.00 [MMOL),] 1-hydroxy-7- [AZABENZOTRIAZOLE] (HOAT, 3.00 [MMOL),] and 1-methylpiperazine (2.00 [MMOL)] in DMF (0.5 M). The reaction mixture was allowed to stir at room temperature overnight. The solvent was removed, and the residue was dissolved in EtOAc. The solution was washed with 1 N HCI, satd aq [NAHCO3] and brine. It was then dried [(NA2SO4),] filtered, and concentrated to obtain the crude product as a viscous oil, which was purified on silica gel (40 g; 3-10% methanol (2 M NH3)/dichloromethane), yielding the title compound (1.68 mmol, 47%). Elemental analysis: calculated for [C13H16N4O,] C 63.91, H 6.60, N 22.93 ; found C 63.76, H 6.79, N 22.87. The MS [AND 1H] NMR data matched that of the sample prepared above.

According to the analysis of related databases, 1H-Benzimidazole-2-carboxylic acid, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2004/22060; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3034-42-2, Adding a certain compound to certain chemical reactions, such as: 3034-42-2, name is 1-Methyl-5-nitroimidazole, 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 3034-42-2.

In a sealed glass tube, formaldehyde (1 g, 33.54 mmol) and 1-Methyl-5-nitro-1H-imidazole (4a) (1 g, 7.8 mmol) solution were added in DMSO (5 mL). The tube was heated at 140 C for 48 h. After that solution was poured into water (5 mL) and extracted with ethyl acetate (3 x 5 mL). Then mixture was dried (MgSO4) and solvent evaporation under vacuum, gave crude in the form of solid, which was recrystallized (THF/heptane, 1:1) and product (5a) was isolated (0.76 g, 62% yield) as white powder; m.p. 117 C.

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-Methyl-5-nitroimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Samant, Bhupesh S.; Sukhthankar, Mugdha G.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 3; (2011); p. 1015 – 1018;,
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 71759-89-2 as follows. 71759-89-2

N,N’-Dimethylsulfonamide chloride (550 muL, 5.16 mmol) was added to a stirring solution of 4-iodoimidazole (500 mg, 2.58 mmol) and TEA (0.90 mL, 6.44 mmol) in ACN (5 mL) at room temperature. After 2 hours, the mixture was concentrated on silica and subjected to flash column chromatography (10-40% EtOAc/hexane gradient) to afford 4-iodo-imidazole-1-sulfonic acid dimethylamide as white solid (620 mg, 80%). 1H NMR (CDCl3, 300 MHz) delta 1.34 (s, 6H), 5.78 (s, 1H), 6.23 (s, 1H); MS (ESI) m/z=301.9 (MH+).

According to the analysis of related databases, 71759-89-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Genelabs Technologies, Inc.; US2010/204265; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common compound: 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 705-09-9

A mixture of 2-difluoromethyl-lH-benzimidazole (7.57 g), 2,4-dichloro-6-morpholinopyrimidine (11.7 g), sodium bicarbonate (21 g) and DMF (100 ml) was stirred under nitrogen and heated to 110C for 20 hours. The resultant mixture was cooled, filtered and the filtrate was evaporated. The resultant product was purified by column chromatography on silica using increasingly polar mixtures of ethyl acetate and methylene chloride as eluent. The solid so obtained was a mixture of major and minor isomeric products. The solid was washed with a mixture of isohexane (400 ml) and diethyl ether (400 ml). The washings were evaporated to give a Residue [A]. The washed solid was recrystallised from warm methylene chloride (30 ml) by the addition of isohexane (120 ml). The resultant crystalline solid was isolated and washed with a mixture of diethyl ether (300 ml) and isohexane (300 ml) and the washings were again evaporated to give a Residue [B]. Residues [A] and [B] were combined and purified using a Waters ‘Xterra’ preparative reversed-phase column (5 microns silica, 19 mm diameter, 100 mm length) using decreasingly polar mixtures of water [containing 1% aqueous ammonium hydroxide (d = 0.88)] and acetonitrile as eluent. There was thus obtained a sample of the minor isomeric product, namely 2-chloro- 4-(2-difluoromethylbenzimidazol-l-yl)-6-morpholinopyrimidine (0.173 g); NMR Spectrum: (DMSOd6) 3.73 (s, 8H), 7.2 (s, IH), 7.44-7.52 (m, 2H), 7.51 (t, IH), 7.77-7.79 (m. IH), 7.88-7.90 (m, IH); Mass Spectrum: M+H+ 366.

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, 705-09-9, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BUTTERWORTH, Sam; GRIFFEN, Edward, Jolyon; PASS, Martin; WO2008/32060; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem