Category: imidazoles-derivatives

Electric Literature of 288-32-4, 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. 288-32-4, name is 1H-Imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1. To a solution of 1 (20 g, 108.1 mmol) in dry DMF (200 mL) were added lH-imidazole (8.1 g, 118.9 mmol), Cs2C03 (38.7 g, 118.9 mmol), Cul (2 g), 18-Crown-6 (2 g). The resulting solution was stirred at 80 C for 24 h. The mixture was cooled to RT, treated with water and extracted with EA. The combined extracts were washed with water, brine, dried over anhydrous Na2S04, filtered and concentrated to give a crude oil. The crude product was purified by recrystallization to afford 2 (1 1 g, 59.2 %).

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, 1H-Imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORGE LIFE SCIENCE, LLC; REMISZEWSKI, Stacy; CHIANG, Lillian W.; MURPHY, Eain Anthony; KAYSER, Frank; SUN, Qun; FINK, Sarah Jocelyn; (128 pag.)WO2019/79519; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one, 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. name: 4-Amino-1H-benzo[d]imidazol-2(3H)-one

4-(aminomethyl)-N,N-dimethylbenzenamine 2i (1 g, 6.9 mmol) was dissolved in 40 ml of AcOEt and at 0C triphosgene (2 g, lequiv.) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 20 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound la (1 g, 6.9 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (50 ml) and washed with water (1 X 30 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 350 mg of a white solid. Yield = 16% 1HNMR (DMSO, 200 MHz) delta 2.51 (6H, s), 4.18 (2H, d, J = 5.6 Hz), 6.58 (2H, m), 6.69 (2H, d, J = 8.8 Hz), 6.86 (2H, m), 7.14 (2H, d, J = 8.8 Hz), 8.18 (1H, s), 9.98 (1H, bs), 10.58 (1H, bs); [M+1] 326.5 (C17H19N5O2 requires 325.37).

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.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 7098-07-9, name is 1-Ethyl-1H-imidazole, molecular formula is C5H8N2, 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. Application In Synthesis of 1-Ethyl-1H-imidazole

Step 1: 341 parts of 1-ethylimidazole (manufactured by Tokyo Chemical Industry Co., Ltd.), 319 parts of dimethyl carbonate (manufactured by Tokyo Chemical Industry Co., Ltd.) and 340 parts of methanol (Tokyo Chemical Industry Co., Ltd.) were charged in a stainless steel autoclave equipped with a reflux condenser, And dissolved. Then, the temperature was raised to 140 ° C. The reaction was carried out at a pressure of 0.8 MPa for 30 hours. 1 H-NMR analysis of the reaction product revealed that 1-ethyl-3-methylimidazolium monomethyl carbonate was formed.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7098-07-9, its application will become more common.

Reference:
Patent; SANYO CHEMICAL INDUSTRIES LIMITED; SATOU, YOSHIMI; MURATA, SHINICHI; SEIKE, HIDEO; (20 pag.)JP5848690; (2016); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 288-32-4,Some common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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.

Benzoyl chloride (4.99 g, 35.5mmol) wasadded dropwise to a solution of imidazole (4.83 g, 7.1mmol)in dichloromethane (25 mL). The reaction mixture wasstirred for 3 h, and the resulting precipitate was removedby filtration. The filtrate was washed with cold water (<=5 C,10mL x 3) and concentrated under reduced pressure. Theresidue was purified by bulb-to-bulb distillation (heatertemperature: 160 C, 80 mmHg) to yield 1c (4.33 g, 71%yield) as colorless liquid. 1HNMR (400 MHz, CDCl3,26 C): /ppm 8.07 (t, J = 1.0 Hz, 1H, f ), 7.817.79(m,2H, a), 7.69 (tt, J1 = 7.4 Hz, J2 = 1.8 Hz, 1H, c), 7.587.54(m, 3H, b and d), 7.16 (dd, J1 = 1.8 Hz, J2 = 1.0 Hz, 1H, e). The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings. Reference:
Article; Kohsaka, Yasuhiro; Homma, Kazumasa; Sugiyama, Susumu; Kimura, Yoshikazu; Chemistry Letters; vol. 47; 1; (2018); p. 100 – 102;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 104619-51-4, 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 104619-51-4 as follows.

A solution containing the product from step 1 (8.36 g, 54.2 mmol) and 2-amino-4-nitrophenol (8.74 g, 54.2 mmol) in anhydrous THF (200 mL) was allowed to reflux under N2 for 14 hours. The mixture was cooled to RT, filtered, and the precipitate was washed with THF (cold) then dried in vacuo to afford the desired product (9.0 g), as a yellow solid. MS (ESI) m/e (M+H+): 180. 1H NMR (DMSO) delta: 7.857.96 (m, 3H), 7.52 (d, J=8.8 Hz, 1H).

According to the analysis of related databases, 104619-51-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck Sharp & Dohme Corp.; Coburn, Craig A.; Ludmerer, Steven W.; Liu, Kun; Wu, Hao; Soll, Richard; Zhong, Bin; Zhu, Jian; (155 pag.)US2019/127365; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 288-32-4, A common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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.

Comparative Example 1; Preparation of 2-(1H-imidazol-1-yl)acetic acid (Process Related to WO2005/063717)Reaction flask was charged with imidazole (50 g), dimethylformamide (20 ml), toluene (200 ml), potassium carbonate (90 g) and potassium iodide (5 g). The mixture was stirred for 10 min and methyl chloroacetate (120 g, 97 ml) was added at 25-30 C. over 1.5 hr. The mixture was stirred for 1 hour at 25-30 C., heated to 60-65 C. and was stirred at this temperature for additional 3 hours. The mixture was cooled down to room temperature and ethyl acetate (100 ml) was added. The mixture was stirred for 20 min and upper organic layer was decanted. Ethyl acetate (100 ml) was added to the residue and the mixture was stirred for 20 min. Upper organic layer was decanted and combined with the first one. Water (100 ml) was added to the residue and the mixture was stirred for 30 min. Inorganic salts were filtered off to give after drying 72.6 g of dry cake (content of diacid in dry inorganic cake was 5.8 g (represents 4.3% of theoretical yield). The filtrate was extracted with ethyl acetate (2×100 ml). Aqueous phase 152 ml contain 24.1 g of the diacid (represents 17.8% of theoretical yield). The ethyl acetate layers were combined with previous extracts. Combined ethyl acetate extracts were evaporated to give 50.5 g of brownish oil.

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kas, Martin; Benes, Michal; Pis, Jaroslav; US2010/130746; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference 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.

COMPOUND 12.1.55: N,N-DIETHYL-4-{7-[(4-METHYL-1H-IMIDAZOL-5- YL) METHYL1-6J. 8, 9-TETRAHYDROri31DIOXOLOr4, 5-F] ISOOUINOLIN-6- YL}BENZAMIDE; 4-Methyl-imidazole-5-carboxyaldehyde (76. 4 mg, 0.69 mmol) was added to a solution of INTERMEDIATE 5.1. 15 (122.6 mg, 0.35 mmol) in 1,2-dichloroethane (5 mL) and the reaction mixture stirred at room temperature for 10 min. Sodium triacetoxyborohydride (516 mg, 2.43 mmol) was added followed by N-methyl-2- pyrrolidinone (400 I1L) and the reaction mixture stirred at RT for 18 h. 1 N NaOH (5 mL) was added and the organic solvent removed in vacuo. The residue was extracted with EtOAc (3 x 20 mL) and the organic layer washed with water (20 mL). The organic layer was concentrated in vacuo and the residue purified by flash chromatography on Si02 column (EtOAc: MeOH 95: 5) to afford COMPOUND 12.1. 55 as an oil (35.6 mg, 23%). 1H NMR (500 MHz, CDC13) : 8 1.13 (br s, 3H), 1.25 (br s, 3H), 2.09 (s, 3H), 2.55 (m, 1H), 2. 78 (m, 1H), 3.09 (m, 1H), 3.28 (br s, 2H), 3.34-3. 40 (m, 2H), 3.55 (br s, 2H), 3.59 (d, J 13.5 Hz, 1H), 4. 58 (s, 1H), 5.96 (s, 1H), 6. 21 (d, J 8 Hz, 1H), 6.55 (d, J 8 Hz, 1H), 7.28-7. 32 (m, 4H), 7.36 (s, 1H) ; 13C NMR (125 MHz, CDCl3) : 8 11. 37, 13. 11, 14.42, 22.28, 39.61, 43.64, 45.72, 49.40, 67.41, 101. 30, 106.56, 117. 66,122. 17, 126.56, 129.73, 130.71, 131.73, 133.45, 136.22, 144.81, 145.28, 145.54, 171. 54; (+) LRESIMS m/z 447.20 [M+H] +.

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; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 1179361-84-2, name is Ethyl 1-amino-1H-imidazole-5-carboxylate, molecular formula is C6H9N3O2, 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. Application In Synthesis of Ethyl 1-amino-1H-imidazole-5-carboxylate

Preparation of intermediate II-29; A mixture of intermediate II-30 and NH4CI in 7N NHa/MeOH solution was heated at 90C (sand bath) in a closed vessel for 72h. The reaction was heated at 110C for 24 h. Fresh 7N was added (20 mL) and the reaction was heated at 120C for 5 h. Solvents were evaporated to dryness. The residue was partitioned between EtOAc/water. The organic layer was washed once with water, dried and evaporated to give only 11 mg of residue. The aqueous layer was evaporated to dryness to give 400 mg of a white solid, as a mixture of desired product, intermediate 11-29 and NH4CI salts (yield > 100%) that was used as such in next reaction.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1179361-84-2, its application will become more common.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; MARTINEZ GONZALEZ, Sonia; ALVAREZ ESCOBAR, Rosa Maria; RODRIGUEZ HERGUETA, Antonio; MARTIN HERNANDO, Jose Ignacio; RAMOS LIMA, Francisco, Javier; WO2011/89400; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, 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: C7H7N5

EXAMPLE 36; 3-Cyclopentyl-1-methyl-2-pyridin-2-yl-1H-indole-6-carboxylic acid {1- [6- (5- amino-1,3, 4-oxadiazol-2-yl)-1-methyl-1 H-benzimidazol-2-yl] cyclobutyl} amide; C- (Di-imidazol-1-yl)-methyleneamine (25 mg, 0.16 mmol) was added in a single portion to a solution of compound 35-3 (Example 35) (80 mg, 0.14 mmol) in THF (4 mL). The resulting solution was heated to 70 C for 16 h, after which time a white precipitate was observed. The reaction was then concentrated under reduced pressure, dissolved in 4 mL DMSO and directly purified on a reversed phase Cis, semi-preparative HPLC column (using a solvent gradient from 5% H20 in MeCN to 100% MeCN) to isolate compound 36-1 (compound 1129, Table 1) as a yellow amorphous solid in >95% homogeneity (19 mg, 23% yield). ‘H NMR (400 MHz, DMSO): 5 1.54-1. 67 (m, 2H), 1.79-1. 94 (m, 6H), 1.95-2. 06 (m, 1H), 2.11-2. 23 (m, 1H), 2.74-2. 84 (m, 2H), 3.19-3. 05 (m, 3H), 3.69 (s, 3H), 3.91 (s, 3H), 7.49 (dd, J = 1.8 & 5.7 Hz, 1 H), 7.59-7. 71 (m, 3H), 7.86-7. 92 (m, 2H) 7. 96-8. 01 (m, 1H), 8.06-8. 10 (m, 1H), 8. 10 (s, 1H), 8.78 (d, J = 4.3 Hz, 1H), 9.51 (s, 1H).

The synthetic route of Di(1H-imidazol-1-yl)methanimine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; BOEHRINGER INGELHEIM PHARMA GmbH & CO KG; WO2005/80388; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 16265-04-6, name is 2-Chloro-1H-imidazole, molecular formula is C3H3ClN2, 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 2-Chloro-1H-imidazole

B’-1 (2.05g, 20.0 mmol), B’-2 (3.38 g, 20.0mmol), Pd2(dba)3 (0.18g, 0.2mmol), PtBu3 (0.04g, 0.4mmol) and KOtBu (1.44g , 15.0 mmol) were dissolved in 40 ml of toluene, and the mixture was stirred at 80 C for 4 hours. The reaction mixture was cooled to room temperature, and extracted three times with 50 mL of water and 30 mL of diethyl ether. The combined organic layer was dried over MgSO4 and the solvent was evaporated. The resulting residue was purified by silica column method to obtain Intermediate B-1 (3.86 g, yield 82%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16265-04-6, its application will become more common.

Reference:
Patent; Choi Don-su; Choi Jin-sol; (70 pag.)KR2019/35043; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem