Month: June 2021

Related Products of 16681-59-7, 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. 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 62 (METHOD O); 6,6-Dimethyl-2-[6-(l-methyl-lH-imidazol-2-yl)-2,3-dihvdrobenzo[l,41oxazin-4-yll-6,7- dihydro [ 1 ,31 thiazolo [ 5 A-c] p yridin-4( 5H)-one; A mixture of Intermediate 66 (0.050 g, 0.14 mmol), l-methyl-2-bromoimidazole (0.067 g, 0.4 mmol), tetra-n-butylammonium bromide (0.135 g, 0.4 mmol), Na2CO3 (0.045 g, 0.4 mmol), tetrakis(triphenylphosphine)palladium(0) (0.016 g, 0.014 mmol) and water (1 mL) in TetaF (3 mL) was heated to 1400C under microwave irradiation for 20 minutes. Additional portions of l-methyl-2-bromoimidazole (0.033 g, 0.2 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.016 g, 0.014 mmol) were added, and heating continued for a further 40 minutes. After cooling to r.t., the reaction mixture was concentrated in vacuo, and the residue partitioned between DCM (50 mL) and water (50 mL). The organic fraction was washed with water (50 mL) and brine (50 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by preparative etaPLC (Method 6) to give the title compound (0.002 g, 4%) as a white solid. deltaeta (CDCl3) 8.18 (IH, d, J 1.9 Hz), 7.33 (IH, dd, J8.5 and J 1.9 Hz), 7.02 (IH, d, J 1.3 Hz), 6.98 (IH, d, J 8.5 Hz), 6.89 (IH, d, J 1.1 Hz), 5.10 (IH, br. s), 4.36-4.29 (2H, m), 4.12-4.04 (2H, m), 3.74 (3H, s), 2.80 (2H, s), 1.32 (6H, s). LCMS (ES+) 396.0 (M+H)+, RT 1.66 minutes (Method I).

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

Reference:
Patent; UCB PHARMA S.A.; WO2008/1076; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 13275-42-8, A common heterocyclic compound, 13275-42-8, name is 2-(2-Bromophenyl)-1H-benzo[d]imidazole, molecular formula is C13H9BrN2, 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: 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).

The synthetic route of 13275-42-8 has been constantly updated, and we look forward to future research findings.

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

Adding a certain compound to certain chemical reactions, such as: 20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid, 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 20485-43-2, Formula: C5H6N2O2

To a solution of N4-(3-aminopropyl)-7-(lH-pyrazol-5-yl)quinoline-2,4-diamine, 3 HC1 (30 mg, 0.077 mmol) and 1 -methyl- lH-imidazole-2-carboxy lie acid (19.32 mg, 0.153 mmol) and triethylamine (0.213 mL, 1.532 mmol) in DMF (1 mL) was added T3P (50% in DMF) (97 mg, 0.153 mmol). After stirring the reaction at room temperature overnight the reaction was concentrated under high vacuum. The reaction was diluted with 1 ml of a mixture of 1: 1 DMF: acetic acid and filtered through a syringe filter and purified via preparative LC/MS with the following conditions: Column: XBridge CI 8, 200 mm x 19 mm, 5-mupiiota particles; Mobile Phase A: 5:95 acetonitrile: water with 0.1% trifluoroacetic acid; Mobile Phase B: 95 :5 acetonitrile: water with 0.1% trifluoroacetic acid; Gradient: a 5-minute hold at 0% B, 0-33% B over 25 minutes, then a 5-minute hold at 100% B; Flow Rate: 20 mL/min; Column Temperature: 25 C. Fraction collection was triggered by MS signals. Fractions containing the desired product were combined and dried via centrifugal evaporation to give N-(3-((2-amino-7-(lH-pyrazol-5-yl)quinolin-4- yl)ainino)propyl)-l-methyl-lH-imidazole-2-carboxarnide as the bis-triflouroacetate salt (7.1 mg, 15 %). NMR (500 MHz, DMSO-de) delta 8.44 (br s, 1H), 8.22 (br d, J=8.7 Hz, 1H), 8.02 (br s, 1H), 7.93 (br s, 1H), 7.90 – 7.76 (m, 3H), 7.55 (br s, 1H), 7.30 (s, 1H), 6.99 (s, 1H), 6.87 – 6.80 (m, 1H), 5.85 (s, 1H), 3.94 (s, 3H), 2.01 – 1.93 (m, 2H). Four protons from sidechain missing, likely due to overlap with suppressed water peak. LC RT: 1.01 min. M/Z=391.1

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

Reference:
Patent; INNATE TUMOR IMMUNITY, INC.; O’MALLEY, Daniel; GAVAI, Ashvinikumar V.; GILL, Patrice; TARBY, Christine M.; WATTERSON, Scott Hunter; GONG, Hua; WILLIAMS, David K.; GHOSH, Shomir; ROUSH, William R.; (307 pag.)WO2019/14402; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 5955-72-6, These common heterocyclic compound, 5955-72-6, name is 2-Chloro-6-nitro-1H-benzo[d]imidazole, 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.

[0635] A mixture of 2-chloro-5-nitro-benzimidazole (985 mg, 5.0 mmole) and 1-(3-aminopropyl)-imidazole (1.8 mL, 3 eq) in toluene (15 mL) was heated at reflux for 5 hr. The reaction was partitioned between EtOAc and brine to give a precipitate that was collected by filtration. Flash chromatography of this material (silica gel; stepwise gradient elution with mixtures of DCM containing 1, 2, 3, . . . 10% MeOH) afforded 2-[3-[imidazo-1-yl]-propylamino]-5-nitro-benzimidazole (550 mg) as a solid. This material was combined with 10% Pd on charcoal (500 mg), suspended in EtOH, and stirred under a hydrogen atmosphere (balloon) overnight. Removal of the catalyst by filtration and the solvent under reduced pressure left the crude 5-amino-2-[3-imidazo-1-ylpropylamino]-benzimidazole as a solid. A portion of this material (77 mg, 0.30 mmole) was added to a mixture of 319A (99 mg, 1.0 eq), an aqueous solution of HCl (0.60 mL, 1.0 M, 2 eq) and n-BuOH (1.5 mL). This was heated in a sealed vial at 120 C. for 20 hr. After cooling to RT, 572 (HPLC retention time (YMC ODS S7 3×50 mm): 1.20 min) was isolated by preparative HPLC.

The synthetic route of 5955-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Das, Jagabandhu; Padmanabha, Ramesh; Chen, Ping; Norris, Derek J.; Doweyko, Arthur M.P.; Barrish, Joel C.; Wityak, John; Lombardo, Louis J.; Lee, Francis Y.F.; US2004/54186; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 17289-26-8, 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. 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a 0.2 M solution of intermediate (l-36a) in THF was added 1.1 eq 1 -methyl- 1 H-imidazole-4-carbaldehyde (Ryan Scientific, Inc., Mt. Pleasant, SC), and this solution was then cooled to 0 C. To this solution was added 0.5 equivalents of potassium t- butoxide as a 1 M solution in THF, and the reaction was allowed to slowly warm to RT. After 18h the solution was acidified with 1 N HCI, brine was added, and extracting three times with ethyl acetate. The resulting organic layers were then combined, dried over sodium sulfate and concentrated to afford crude (l-36b). This material was taken forward crude.

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-1H-imidazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; BENBOW, John William; LOU, Jihong; PFEFFERKORN, Jeffrey Allen; TU, Meihua Mike; WO2010/29461; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1231930-33-8, These common heterocyclic compound, 1231930-33-8, name is 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole, 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.

Under nitrogen protection, 24 palladium acetate (28 mg) and 25 tricyclohexylphosphine (54.3 mg) was added into the solution of 26 6-bromo-4-fluoro-1-isopropyl-2-methyl-H-benzo[d]imidazole (300 mg, 1.10 mmol), 27 bis(pinacolato)diboron (422 mg, 1.70 mmol) and 28 potassium acetate (326 mg, 3.3 mmol) in anhydrous 29 dimethyl sulfoxide (DMSO, 5 mL), and the reaction was carried out at 100 C. under nitrogen protection for 2 hours. After cooling to room temperature, the reaction was filtered on Celite, the filter cake was washed with ethyl acetate, the filtrate was washed with brine, dried over anhydrous sodium sulfate, the filtrate was concentrated under reduced pressure, and the filtrate was separated on column chromatography (eluant:petroleum ether/ethyl acetate (v/v)=3:1), to affard 260 mg of a pale yellow solid. Yield: 74.3%. LC-MS(APCI): m/z=319.3 (M+1).

The synthetic route of 1231930-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenzhen TargetRx, Inc.; Wang, Yihan; Ren, Xingye; Jin, Jian; Li, Huanyin; Ai, Yixin; (162 pag.)US2019/152954; (2019); 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. 1467-16-9, name is 1H-Imidazole hydrochloride, A new synthetic method of this compound is introduced below., Recommanded Product: 1467-16-9

A mixture of lithium(1+) ion 3-amino-7-chloro-5/-/-pyrrolo[2,3- 5]pyrazine-2-carboxylate, Intermediate 12 (90 mg, 0.45 mmol), CDI (1 10 mg, 0.67 mmol) and 1 /-/-imidazole hydrochloride (1 : 1) (56 mg, 0.53 mmol) in DMF (2 ml) was stirred at RT for 1 h. Additional CDI (50 mg, 0.31 mmol) was added and the reaction was allowed to continue for a further 1 h. The reaction mixture was diluted with water (4 ml) then filtered. The solid was washed with water then dried under vacuum to afford the product as a yellow solid (83 mg, 75%). 1 H NMR (500 MHz, DMSO-cfe) delta 1 1.37 (s, 1 H), 8.84 (s, 1 H), 8.00 (t, J = 1.4 Hz, 1 H), 7.45 (s, 2H), 7.41 – 7.37 (m, 1 H), 7.12 – 7.08 (m, 1 H), 2.22 (d, J = 1.1 Hz, 3H). LC/MS (System A): m/z (ESI+) = 243 [MH+], Rt = 0.78 min, UV purity = 98%.

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; ENTERPRISE THERAPEUTICS LIMITED; MCCARTHY, Clive; HARGRAVE, Jonathan, David; HAY, Duncan, Alexander; SCHOFIELD, Thomas, Beauregard; WENT, Naomi; (261 pag.)WO2018/96325; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 25676-75-9, 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. 25676-75-9, name is 4-Bromo-1-methylimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A deaerated mixture of 4-bromo-1-methyl-1H-imidazole (10) (0.800g, 5.00mmol), an arylboronic acid 7 (10.0mmol), CsF (2.28g, 15.0mmol), PdCl2(dppf) (0.183g, 0.25mmol), and BnEt3NCl (0.057g, 0.25mmol) in toluene (30mL) and water (30mL) was heated at reflux under argon for 48h. The mixture was then cooled to room temperature and partitioned between water and AcOEt, and the organic extract was dried and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel to provide the desired product. This procedure was used to prepare compounds 9a and 9b, both in 95% yield.

The synthetic route of 4-Bromo-1-methylimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bellina, Fabio; Guazzelli, Nicola; Lessi, Marco; Manzini, Chiara; Tetrahedron; vol. 71; 15; (2015); p. 2298 – 2305;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1003-21-0, 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 1003-21-0 as follows.

Step 2: Formation of 2-(4-{2-[3-(3-Methyl-3H-imidazol-4-yl)-phenyll-pyrimidin-5-yl)- pyrazol-i -yl)-i-pyrrolidin-1-yl-ethanone A mixture of 1 -Pyrrolidin- 1 -yl-2-(4-{2-[3-(4,4,5,5-tetramethyl-[i ,3,2]dioxaborolan-2-yl)- phenyl]-pyrimidin-5-yI}-pyrazol-1-yl)-ethanone (4 mL of the solution obtained in step 1), 5-bromo-1-methyl-1H-imidazole (35 mg; 0.22 mmol; 1.0 eq.), Pd(Ph3)4 (13 mg; 0.01mmol; 0.05 eq.) and potassium carbonate (90 mg; 0.65 mmol; 3.0 eq.) in water (0.73 mL) was heated at 120C in MW for 30 mm. Addition of 5-bromo-1-methyl-1H-imidazole (35 mg; 0.22 mmcl; 1.0 eq.) and heating at 120C for 30 mm had to be repeated twice to complete the reaction. The reaction mixture was then diluted with water and extracted twice with EtOAc. Combined organic phases were washed with brine, dried overmagnesium sulfate, filtered and concentrated. Purification by flash chromatography on silica (DCM:MeOH, gradient from 100:0 to 80:20) gave a black gum which was redissolved in DCM. Addition of cyclohexane afforded a brown precipitate which was filtered and dried under vacuum to give the title compound as a beige solid (40 mg, 44%). 1H NMR (300 MHz, DMSO-d6) d 9.20 (s, 2H), 8.47-8.46 (m, 1H), 8.41-8.37 (m,2H), 8.14 (d, J= 0.6 Hz, 1H), 7.76 (s, 1H), 7.68-7.60 (m, 2H), 7.15 (s, 1H), 5.12 (s, 2H),3.74 (s, 3H), 3.52 (t, J= 6.8 Hz, 2H), 3.32 (t, J= 6.8 Hz, 2H), 1.93 (quint., J= 6.8 Hz, 2H),1.80 (quint., J= 6.8 Hz, 2H). HPLC (Condition A): Rt 2.21 mm (purity 96.2%). MS (ESI+):414.4.

According to the analysis of related databases, 1003-21-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARES TRADING S.A.; CROSIGNANI, Stefano; JORAND-LEBRUN, Catherine; GERBER, Patrick; MUZERELLE, Mathilde; WO2014/8992; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 615-15-6, 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 615-15-6 as follows.

General procedure: A solution of 10.0 mmol of compound 1a-1d in 14 mL of concentrated sulfuric acid was heated to 100-105C, 14 mL (0.26 mol) of 30% aqueous hydrogen peroxide was added dropwise with stirring,and the mixture was stirred for 1 h at 130C. After cooling, the mixture was poured into water and adjusted to pH 4, and the precipitate was filtered off.

According to the analysis of related databases, 615-15-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Brusina; Nikolaev; Ramsh; Piotrovskii; Russian Journal of Organic Chemistry; vol. 52; 10; (2016); p. 1528 – 1530; Zh. Org. Khim.; vol. 52; 10; (2016); p. 1533 – 1535,3;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem