Month: March 2021

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. 405173-97-9, name is 2-(2-Chloroethyl)-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C9H9ClN2

General procedure: 2-(2-Aminoethyl)-N-[(3-fluoropyridin-2-yl)methyl]-1 ,3-thiazole-4-carboxamide dihydrochloride (103) (2.0 g, 3.96 mmol) was added to a solution of 2-(2-chloroethyl)-1 H-1 ,3-benzodiazole hydrochbride (1.12 g, 5.15 mmol) and DIPEA (10.6 ml, 59.45 mmol) in DMF (60 ml). The reaction mixture was allowed to stir at 3GC for 6 d (reaction was monitored by LCMS). The mixture was concentrated in vacuo and the residue was neutralised using sat. NaHC03 (aq). The aqueous layer was extracted using 4: 1 CHCb / 1 PA (4 x 100 ml) and the combined organic layers were dried (MgS04), filtered and evaporated in vacuo. The crude residue was purified by flash column chromatography (kp-NH, eluting with a gradient of 60-100% EtOAc / heptane followed by 0-20% MeOH / EtOAc) follow by neutral reverse-phase column chromatography (gradient elution 0-60% MeCN / water) to give the title compound (0.173 g, 10%) as a yellow oil. 1 H-NMR (Methanol-d4, 500 MHz): d[ppm]= 8.31 (d, J = 4.6 Hz, 1 H), 8.02 (s, 1 H), 7.57 (t, J = 9.1 Hz, 1 H), 7.45 – 7.40 (m, 2H), 7.36 (dd, J = 8.6, 4.3 Hz, 1 H), 7.17 (dd, J = 6.0, 3.2 Hz, 2H), 4.68 (s, 2H), 3.26 (d, J = 6.8 Hz, 2H), 3.15 – 3.07 (m, 6H) HPLCMS (Method D): [m/z]: 425.1 [M+H]+In a similar fashion to general procedure 7, -(pyridin-2-ylmethyl)-4H,5H,6H,7H-thieno[2,3-c]pyridine-3- carboxamide (450) (65 mg, 0.24 mmol), K2C03 (49 mg, 0.36 mmol) and 2-(2-chloroethyl)-1 H- benzimidazole (47 mg, 0.26 mmol) in acetone (3 ml) at room temperature for 24 h, followed by the addition of DMF (5 ml), Nal (39 mg, 0.26 mmol), DIPEA (0.16 ml, 0.95 mmol) and 2-(2-chloroethyl)-1 H- benzimidazole (94 mg, 0.52 mmol) at room temperature for 72 h, gave the title compound (9 mg, 9%) as an orange solid after purification by basic prep-HPLC. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.17 (s, 1 H), 8.75 (t, J = 6.0 Hz, 1 H), 8.50 (d, J = 4.2 Hz, 1 H), 7.94 (s, 1 H), 7.75 (td, J = 7.7, 1.8 Hz, 1 H), 7.46 (s, 2H), 7.31 (d, J = 7.8 Hz, 1 H), 7.28- 7.23 (m, 1 H), 7.10 (dd, J = 6.0, 3.1 Hz, 2H), 4.48 (d, J = 6.0 Hz, 2H), 3.71 (s, 2H), 3.05 (t, J = 7.2 Hz, 2H), 2.96 (t, J = 7.2 Hz, 2H), 2.82 (d, J = 5.3 Hz, 2H), 2.75 (t, J = 5.7 Hz, 2H) HPLCMS (Method B): [m/z]: 418.2 [M+H]+

The synthetic route of 405173-97-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIFOR (INTERNATIONAL) AG; DUeRRENBERGER, Franz; BUHR, Wilm; BURCKHARDT, Susanna; BURGERT, Michael; KALOGERAKIS, Aris; REIM, Stefan; MANOLOVA, Vania; BOYCE, Susan; YARNOLD, Christopher John; PENA, Paula; SHEPHERD, Jon; LECCI, Cristina; JARJES-PIKE, Richard; SCOTT, John; (416 pag.)WO2017/68089; (2017); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H6N4S

To a stirred solution of 6.8 g (35.0 mmol) of (5) in 150 mL of CH2Cl2 at RT was added 6.4g(35mmol) of l .l’-thiocarbonyldiimidazole. The mixture was stirred at room temperature for 15 minutes and then evaporated under reduced pressure and the residue was passed through a short pad of silica gel, eluting with a gradient of hexane/EtOAc, which gave (5-Isothiocyanato-2-methoxy- phenyl)-methyl-propyl-amine (6) (7.85g, 95%) as a colorless oil.

According to the analysis of related databases, 6160-65-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; WO2007/140002; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, molecular formula is C4H5ClN2O2S, 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: 1-Methyl-1H-imidazole-4-sulfonyl chloride

Example 227 1-methyl-N-[3-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4-phenoxyphenyl]-1H-imidazole-4-sulfonamide [1006] The product from Example 225C (0.044 g, 0.15 mmol), 1-methyl-1H-imidazole-4-sulfonyl chloride (0.033 g, 0.180 mmol) and triethylamine (0.042 mL, 0.30 mmol) were combined in dichloromethane (0.75 mL), heated at 60 C. for 2 hours and concentrated. Purification by chromatography (silica gel, 0-3% methanol in dichloromethane) afforded the title compound (0.038 g, 56%). 1H NMR (300 MHz, DMSO-d6) delta 10.21 (s, 1H) 7.84 (d, J=1.36 Hz, 1H) 7.75-7.78 (m, 2H) 7.48 (dd, J=9.49, 2.71 Hz, 1H) 7.25-7.35 (m, 2H) 7.21 (d, J=2.71 Hz, 1H) 7.09 (dd, J=8.82, 2.71 Hz, 1H) 7.03 (t, J=7.46 Hz, 1H) 6.89 (d, J=8.82 Hz, 1H) 6.83 (d, J=7.80 Hz, 2H) 6.37 (d, J=9.49 Hz, 1H) 3.67 (s, 3H) 3.43 (s, 3H). MS (ESI+) m/z 437 (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 137049-00-4, its application will become more common.

Reference:
Patent; HUBBARD, Robert D.; WANG, Le; PARK, Chang H.; SUN, Chaohong; McDANIEL, Keith F.; PRATT, John K.; SOLTWEDEL, Todd N.; WENDT, Michael D.; HOLMS, John H.; LIU, Dachun; SHEPPARD, George S.; US2013/331382; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, 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. Formula: C5H6N2O

General procedure: Into a round-bottom flask, equipped with a condenser and containing a suspension of 6 (2.0 mmol, 1 equiv) in ethanol (15 mL), was introduced the aldehyde (2.2 mmol, 1.1 equiv) and two drops of concentrated HCl. The reaction mixture was stirred and heated at 80 C for approximately 18 h. While cooling down the crude mixture in an ice bath, a precipitate was formed which was subsequently filtered off and washed with both water (2 ¡Á 10 mL) and cold ethanol (3 ¡Á 15 mL). The solid residue was then dried in vacuum at 60 C.

The synthetic route of 1-Methyl-1H-imidazole-5-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pevet, Isabelle; Brule, Cedric; Tizot, Andre; Gohier, Arnaud; Cruzalegui, Francisco; Boutin, Jean A.; Goldstein, Solo; Bioorganic and Medicinal Chemistry; vol. 19; 8; (2011); p. 2517 – 2528;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

71759-89-2, name is 5-Iodo-1H-imidazole, 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. Application In Synthesis of 5-Iodo-1H-imidazole

General procedure: Method A: In a20 mL microwave Biotage tube, a mixture of 4-iodo-1H-imidazole(1a) (0.194 g, 1.0 mmol), a boronic acid 2(2.0 mmol), CsF (0.456 g,3.0 mmol), PdCl2(dppf)(0.041 g, 0.05 mmol) and BnEt3NCl(0.011 g, 0.05 mmol) in toluene(7 mL) and water (7 mL)was purged with argon andheated under microwaveirradiation. When the reaction was complete, the mixture was cooled toroom temperature and concentrated under reduced pressure. The residue waspurified by flash chromatography on silica gel to provide compounds 3a-3i and 3k-3o in yields ranging from 40 to 91%. Time and temperaturereactions were collected in Table 1.

The synthetic route of 71759-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Vichier-Guerre, Sophie; Dugue, Laurence; Pochet, Sylvie; Tetrahedron Letters; vol. 55; 46; (2014); p. 6347 – 6350;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 128293-62-9, 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. 128293-62-9, name is Ethyl 4-amino-1-methyl-1H-imidazole-2-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To Im-3 (0. 38 g) in DMF (8 mL) and Hunig’s base (2ML) was added ditert-butyl dicarbonate (0.7 ml) and the mixture stirred at 60 C for 3 hr. It was then cooled to room temperature and brine (6 ML) and ethyl ether (6 ML) were added. The ether layer was extracted with 10% citric acid, brine, saturated sodium bicarbonate, and brine (10 mL each). The ether layer was then dried over sodium sulfate and evaporated under vacuum. NAOH (1M, 5mL) in methanol was then added and solution stirred at 60 C for 1 hr. The mixture was then cooled to 0 C and neutralised with 1M HC1 to pH 2 at which a white gel was formed. The gel was collected by gravity filtration and washed with water pH=6 before it was freeze dried to yield the product as a white powder. Yield (0.41 g, 76%). 1H NMR (DMSO): 6 9.45 (bs, 1H, NH), 7.21 (bs, 1H), 3. 86 (s, 3H), 3.67 (bs, 1H, OH), 1.4 (s, 9H).

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

Reference:
Patent; UNIVERSITY OF WESTERN SYDNEY; WO2005/33077; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 71759-87-0, These common heterocyclic compound, 71759-87-0, name is 4-Iodo-1-methyl-1H-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.

Procedure E3c – {3-r7-(1-Methyl-1 H-imidazol-4-yl)-imidazori ,2-alpyridin-3-yll-phenyl}-3-(2.2,2-trifluoro-ethyl)-urea; Procedure E3c is using the conditions described in generic Suzuki A4eTo a stirred mixture of 1-[3-(7-Boronic acid -imidazo[1 ,2-a]pyridn-3-yl)-phenyl]-3-(2,2,2- trifluoro-ethyl)-urea (0.15g, 0.39 mmol), in a MW tube was added 4-iodo-1-methyl-1 H- imidazole (83mg, 0.39mmol), SPHOS (6.5mg, 0.016mmol) and Pd2(dba)3 (7mg, 0.0076mmol ) in dioxane (2ml) followed by K3PO 4 (252mg, 1.18mmol) in water (1.2ml). The reaction mixture was heated in a CEM discover microwave synthesizer (300W) at 120 0C for hr. The mixture was allowed to cool, then partitioned between EtOAc /H2O, the organic layer was separated, dried (MgSO4), filtered and the solvent removed in vacuo. The residue was purified by prep HPLC to afford the desired product (8mg) MS: [M+H]+ = 415.To a stirred mixture of 1-[3-(7-Boronic acid -imidazo[1 ,2-a]pyridn-3-yl)-phenyl]-3-(2,2,2- trifluoro-ethyl)-urea (0.15g, 0.39 mmol), in a MW tube was added 4-iodo-1-methyl-1 H- imidazole (83mg, 0.39mmol), SPHOS (6.5mg, 0.016mmol) and Pd2(dba)3 (7mg, 0.0076mmol ) in dioxane (2ml) followed by K3PO 4 (252mg, 1.18mmol) in water (1.2ml). The reaction mixture was heated in a CEM discover microwave synthesizer (300W) at 120 0C for hr. The mixture was allowed to cool, then partitioned between EtOAc /H2O, the organic layer was separated, dried (MgSO4), filtered and the solvent removed in vacuo. The residue was purified by prep HPLC to afford the desired product (8mg) MS: [M+H]+ = 415.

Statistics shows that 4-Iodo-1-methyl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 71759-87-0.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/78091; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 64591-03-3, These common heterocyclic compound, 64591-03-3, name is 2,5-Dibromo-1H-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.

General procedure: To a stuffed solution of 2,4-dibromothiazole (2) (4 mmol) in dimethylformamide (DMF) (15 mL), the coffesponding amine (1) (4 mmol) and diisopropylethylamine (DIPEA) (1.55 g, 2 mL, 12 mmol) were added under a stream of nitrogen.The reaction mixture was stirred at 80C for 4-10 h (monitored by Thin-layer chromatography (TLC)), then cooled to room temperature (rt), quenched with cold water (H20) (50 mL) and extracted with ethyl acetate (EtOAc) (3×30 mL). The combined organic layer was washed with H20 (2×10 mL), dried over sodium sulfate and concentrated to give the crude compound 3. The resulting product 3, the corresponding imidazole 4 (12 mmol),palladium(II)bis(triphenylphosphine) diacetate (Pd(OAc)2(PPh3)2) (0.1 mmol) and toluene (50 mL) were refluxed for 24 h. After cooling, the organic solvent was removed under vacuum. The resulting residue was purified by preparative high-performance liquid chromatography (HPLC) (EtOAc – Hexane (1:5) as eluent) to give the final product 5 as a solid. It was additionally purified by reverse phase HPLC (gradient acetonitrile (MeCN) – H20, 20 to 80% of MeCN aseluent). A compound of formula S are examples 1-15, 17-22, 24-40, 42-50 and 52-62.

The synthetic route of 64591-03-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; THE UNIVERSITY OF BRITISH COLUMBIA; BAN, Fuqiang; DALAL, Kush; FLOHR, Alexander; LEBLANC, Eric J. J.; LI, Huifang; RENNIE, Paul S.; TCHERKASSOV, Artem; (57 pag.)WO2018/114781; (2018); A1;,
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. 57090-88-7, name is 1H-Imidazole-4-carbonitrile belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 57090-88-7

A 22-L, four-neck, round-bottom flask equipped with a mechanical stirrer, a temperature probe, and an addition funnel with a nitrogen inlet was charged with IH- imidazole-4-carbonitrile (830 g, 8.91 mol, as prepared in the previous step), potassium carbonate (2.47 kg, 17.8 mol), and acetone (6.0 L). Agitation was initiated and the mixture was cooled to 10 0C with an ice bath. SEMCl (1.50 kg, 9.00 mol) was added through the addition funnel over 210 min to maintain the internal temperature below 15 0C. The reaction was then allowed to warm to ambient temperature and stirred at ambient temperature overnight (20 h). The reaction mixture was then cooled in an ice bath to 10 0C and quenched by the slow addition of water (8.0 L) over 30 min to maintain the internal temperature below 30 ¡ãC. The resulting mixture was transferred to a 22-L separatory funnel and extracted with ethyl acetate (2 x 7.0 L). The combined organics were concentrated under reduced pressure at 35 0C to give the crude product as a dark brown oil, EPO which was purified through a plug of silica gel (16.5 x 20 cm, 2.4 kg silica gel) using 2:1 heptane/ethyl acetate (15 L) as eluent. The fractions containing the product were combined and concentrated under reduced pressure at 35 0C to afford a mixture of the title compounds as a light brown oil [1785 g, 90percent). The 1H NMR spectrum was consistent with the assigned structure and indicated the presence of a 64:36 ratio of regioisomers.

The synthetic route of 57090-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2006/47277; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 89830-98-8, A common heterocyclic compound, 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, molecular formula is C6H8N2, 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.

[0345] A mixture of Example 13a (600 mg, 5.55mmol) and Example 13b (400 mg, 1.65 mmol) Cul (45 mg, 0.24 mmol), K3P04 (1 g, 4.7 mmol), 4,7-Dihydroxy-l,10-phenanthroline (cas: 3922-40-5, 90 mg, 0.42 mmol), TBAB (386 mg, 1.2 mmol) in H20 (10 mL) under N2 was heated at 100 oC overnight. After cooling, filtered and concentrated under reduced pressure to give the crude and further purified by silica gelchromatography to give the product 200 mg as yellow solid. LCMS [M+1] + =271.0

The synthetic route of 89830-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (227 pag.)WO2018/151830; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem