Tag: M.W=100-200

Some common heterocyclic compound, 5098-11-3, name is 5-Amino-1H-imidazole-4-carbonitrile, molecular formula is C4H4N4, 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: C4H4N4

Example 37: General procedure for the preparation of 4-methoxy-benzoyl- imidazo[1 ,5-a]pyrimidines of general formula (I) following Scheme 1.N-[3-[8-(4-methoxy-benzoyl)-imidazo[1 ,5-a]pyrimidin-4-yl]-phenyl]-N-methyl- methanesulfonamidePart A A solution of 4-methoxy-phenyl magnesium bromide was prepared from 1.0 g (42 mmol) of magnesium and 7.9 g (42 mmol) of 1 -bromo-4-methoxy-benzene in 40 ml of dry tetrahydrofuran.To the solution of the Grignard reagent, cooled by an ice-salt bath, a mixture of 1 g (9.3 mmol)of 5-amino-1 H-imidazole-4-carbonitrile and 20 ml of dry tetrahydrofuran was slowly added with stirring. After standing at room temperature for 2 hours, the mixture was cooled and decomposed by adding, with stirring, 40 ml of 3M hydrochloric acid. When the decomposition was completed (1 hour at a temperature between 90-950C), the reaction mixture was basified to ph 10 with 25% ammonium hydroxide and was extracted with methylene chloride. The solution was dried with anhydrous sodium sulfate and the methylene chloride was distilled under diminished pressure to yield an oil which was chromatographied (silica gel) using methylene chloride/methanol as eluent to produce 1.52 g (yield 77%) of (5-amino-1 H- imidazol-4-yl)-(4-methoxy-phenyl)-methanone. 1H NMR (400 MHz, CDCI3): 3.85 (3H, s), 5.41 (1 H, b), 6.69 (2H, d, J= 8.4 Hz), 7.3 (1 H, s), 7.81 (2H, d, J= 8.4 Hz). MS (ES) m/z = 218 (MH+) HPLC = 91%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5098-11-3, its application will become more common.

Reference:
Patent; FERRER INTERNACIONAL, S. A.; WO2006/84835; (2006); A1;,
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 6953-65-7 as follows. category: imidazoles-derivatives

A mixture of (5-Chloro-1 H- benzoimidazol-2-yl)-methanol (3.8 g) suspended in 2 N sodium carbonate (110 mL) was treated with a solution of [KMN04] (4.935 g in 310 mL of water). The resulting mixture was heated to [100 C] for 2 h and then filtered. The filtrate was cooled to room temperature, and the solution was adjusted to acidic pH, via addition of 3 N acetic acid, to afford a precipitate. The solid material was isolated by filtration, washed with water and dried under vacuum to give the title intermediate (2.910 g). This material was used in Step C without further purification.

According to the analysis of related databases, 6953-65-7, 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

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. 169770-25-6, name is Methyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C6H7N3O4

Methyl l-methyl-4- nitroimidazole-2-carboxylate 40 (3.3 g, 17.8 mmol), dissolved in 1 : 1 MeOH:EtOAc (100 niL), was shaken with hydrogen at 70 psi, for 14 h in presence of Pd/C (400 mg). The reaction mixture was filtered through a bed of celite. The celite was washed with MeOH and the filtrate was concentrated under reduced pressure to furnish crude amine as black oil. The residue was taken up in benzene and concentrated to furnish the amine as black solid, filtered and washed with ether (2.5 g, 88%). The crude amine was dissolved in CH3CN (50 mL) and DIEA (2.3, 18 mmol). A solution of 1- methyl-2-trichloroacetylimidazole 24 (3.6 g, 14.7 mmol) in CH3CN (50 mL) was added to the amine solution at 0 0C. The reaction mixture was allowed to stir for 10 h, solvent was removed and the residue was taken up in MeOH and the product was precipitated by addition Of Et2O to furnish desired compound 41 (2.13 g, 68%). 1H- NMR (DMSO-d6) deltaltheta.1 1 (s, exch, IH, NH), 7.69 (s, IH, Im’-C5H), 7.43 (s, IH, Im- C5H), 7.07 (s, IH, Im-C4H), 3.99 (s, 3H, CH3), 3.97 (s, 3H, CH3), 3.82 (s, 3H, OCH3). 13C-NMR (75 MHz, DMSO-d6) 6159.4 (+, s, CO), 157.2 (+, s, CO), 138.9 (+, s, Im- C2), 137.2 (+, s, Im-C2), 132.4 (+, s, Im-C4), 128.9 (-, d, Im-C4), 127.7 (-, d, Im-C5), 117.3 (-, d, Im-C5), 61.9 (+, t, -OCH2-), 37.6 (-, q, CH3), 35.8 (-, q, CH3), 14.2 (-, q, CH3). EI-HRMS: m/z calcd for C1 1H13N5O3 263.1018; found 263.1016 (M+, 100%), 204.0888 (27%), 182.0573 (27%), 150.0301 (30%), 109.0393 (26%).

The synthetic route of 169770-25-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF SASKATCHEWAN; WO2007/45096; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 29518-68-1, name is 2-(1H-Benzo[d]imidazol-2-yl)ethanamine, 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: C9H11N3

Step 2; N3-[4-[2-(Benzimidazol-2-yl)ethyl)aminomethylbenzoyl)-N2-Cbz-L-2,3-diaminopropionic acid on 2-chlorotrityl resin; [Show Image] Shake the resin (Preparation 4, Step 1) (0.8 g, 0.4 mmol) and 2-[2-(aminoethyl)]benzimidazole (3.25 g) in DMF (25 mL) in a sealed vial for 44 hours. Transfer resin to funnel apparatus, and wash the resin with DMF (25 mL x 5) and then CH2Cl2 (20 mL x 5) to give the title resin.

The synthetic route of 2-(1H-Benzo[d]imidazol-2-yl)ethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; EP1135374; (2006); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 89088-69-7, These common heterocyclic compound, 89088-69-7, name is 1-Methyl-1H-imidazol-4-amine hydrochloride, 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.

To a solution of 2,4-dichlorofuro[3,2-d]pyrimidine (la) (0.71 g, 3.74 mmol; CAS 956034- 07-4) in 2-Propanol (20 mL) was added DIPEA (1.63 mL, 9.36 mmol), 1-methyl-1H-imidazol-4-amine hydrochloride (0.5 g, 3.74 mmol) and heated at reflux for 24 h. The reaction mixture was concentrated in vacuum to dryness and the residue obtained was triturated with water. The solid obtained was collected by filtration and dried in vacuum to afford 2-chloro-N-(l-methyl-lH-imidazol-4-yl)furo[3,2-d]pyrimidin-4-amine (lb) (550 mg,59 % yield) as brown solid; NMR (300 MHz, DMSO-^) delta 10.89 (s, 1H, D20exchangeable), 8.35 (d, J = 2.1 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.39 (d, J = 1.3 Hz, 1H), 7.03 (d, J = 2.1 Hz, 1H), 3.71 (s, 3H); MS (ES+): 250.3 (M+l), 272.3, 274.3 (M+Na), (ES-): 248.2 (M-l).

Statistics shows that 1-Methyl-1H-imidazol-4-amine hydrochloride is playing an increasingly important role. we look forward to future research findings about 89088-69-7.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 67768-61-0,Some common heterocyclic compound, 67768-61-0, name is 1-Cyclohexyl-1H-imidazole, molecular formula is C9H14N2, 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.

2,4,5-tribromo-1-cyclohexyl-1H-imidazole (12.2.). N-bromosuccinamide (1.78 g, 9.99 mmol) dissolved in CHCl3 (4 ml) at 0 C. was added to a 4 ml solution of 12.1 (500 mg, 3.33 mmol) in CHCl3. The mixture was stirred at rt for 17 h, filtered, concentrated, and the crude residue stirred in ether for 30 min. Filtration and concentration gave a crude product which was purified by SiO2 chromatography (10% EtOAc/hexanes) to afford 267 mg (21%) 12.2. MS (ESI) 385.0 (MH+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Cyclohexyl-1H-imidazole, its application will become more common.

Reference:
Patent; Glunz, Peter W.; Douty, Brent D.; Martin, Scott W.; Romine, Jeffrey; US2005/75376; (2005); 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. 106429-38-3, name is Methyl 2-amino-1H-benzo[d]imidazole-5-carboxylate, A new synthetic method of this compound is introduced below., name: Methyl 2-amino-1H-benzo[d]imidazole-5-carboxylate

AA. 5-Carboxylic acid-2-aminobenzimidazole (16) 5-Carboxylic acid methyl ester-2-aminobenzimidazole (350 mg, 1.83 mmol, 1.0 eq, 15) was dissolved in a 1:1 mixture of MeOH (10 mL) and water (10 mL) in a 100 mL round bottom flask, and treated with 5.0 M aq. NaOH (10 mL). The reaction mixture was stirred for 12 h at rt, after which the MeOH was removed in vacuo. The aqueous solution was cooled to 0 C., and concentrated aq. HCl was added until pH ?2 was reached. The resulting precipitate was filtered and dried in vacuo at 50 C. to afford the HCl salt of 5-carboxylic acid-2-aminobenzimidazole (16) as a light brown crystalline solid (356 mg, 1.67 mmol, 91% yield). 1H NMR (300 MHz, DMSO-d6) delta 7.45 (d, 1H, J=8.3 Hz), 7.81 (dd, 1H, J=8.4, 1.5 Hz), 7.92 (d, 1H, J=1.4 Hz), 8.90 (s, 2H), 12.99 (bs, 2H); 13C NMR (75 MHz, DMSO-d6) delta 111.1 112.5, 124.7, 125.5, 129.8, 133.2, 151.5, 167.0; EI-MS: calculated m/z [M]+ 177.0533, observed m/z 177.0536.

The synthetic route of 106429-38-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BLACKWELL, Helen; Frei, Reto; Breitbach, Anthony; Lynn, David M.; Broderick, Adam H.; US2013/136782; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 93668-43-0, These common heterocyclic compound, 93668-43-0, name is 2-(1H-Imidazol-1-yl)ethanamine dihydrochloride, 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.

In like manner, the reaction of 1H-imidazole-1-ethaneamine dihydrochloride with 2-furoyl chloride by the procedure of Example 1 provided N-[2-(1H-imidazol-1-yl)ethyl]-2-furanecarboxamide, m.p. 131-133 C.

Statistics shows that 2-(1H-Imidazol-1-yl)ethanamine dihydrochloride is playing an increasingly important role. we look forward to future research findings about 93668-43-0.

Reference:
Patent; American Cyanamid Company; US4489089; (1984); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 279226-70-9, 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. 279226-70-9, name is 1-Methyl-1H-benzimidazole-5-carboxaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A suspension of 6-(l-methyl-lH-pyrazol-4-yl)-4-(6-(piperazin-l-yl)pyridin-3- yl)pyrazolo[l,5-a]pyrazine-3-carbonitrile dihydrochloride (Example 8; 30 mg, 0.078 mmol) in DCE (778 mu.) was treated sequentially with 1 -methyl- lH-benzimidazole-5-carboxaldehyde (25 mg, 0.16 mmol) and NaBH(AcO)3 (49 mg, 0.23 mmol). The mixture was stirred overnight at ambient temperature, and then concentrated in vacuo. The residue was purified first by silica chromatography (using 0-20% MeOH in DCM as the gradient eluent) and then by C18 reverse phase chromatography (using 5-95% ACN/water with 0.1% TFA the gradient eluent) to cleanly afford the title compound as its TFA salt. The TFA salt was treated with saturated NaHCCb(aq), and subsequently extracted into EtOAc (3x). The combined organic extracts were dried over anhydrous Na2S04(S), filtered, and concentrated in vacuo to cleanly afford the title compound (1.5 mg, 3.6% yield). MS (apci) m/z = 529.8 (M+H).

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-benzimidazole-5-carboxaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ANDREWS, Steven W.; BLAKE, James F.; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MORENO, David A.; REN, Li; WALLS, Shane M.; (421 pag.)WO2018/136661; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

93668-43-0, name is 2-(1H-Imidazol-1-yl)ethanamine dihydrochloride, 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: 2-(1H-Imidazol-1-yl)ethanamine dihydrochloride

To a stirred solution of 2-(1H-imidazol-1-yl)ethan-1-amine dihydrochloride (commercially available from Sigma Aldrich) (600 mg, 3.25 mmol) in DMF (5 mL) was added DIPEA (2.2 mL, 13.0 mmol) at 0 C. After 15 min, tert-butyl N-[(1E)-{[(tert-butoxy)carbonyl]amino}(1H-pyrazol-1-yl)methylidene]carbamate (commercially available from Sigma Aldrich) (1.1 g, 3.58 mmol) was added at the same temperature and allowed to stir at RT for 16 h. N2 gas was bubbled into the reaction mixture for 15 minutes then water was added to the crude product followed by stirring for 5 minutes. The resulting precipitate was filtered, washed with water (2 x 10 mL) and dried under high vacuum affording a white solid (800 mg, 71%). M/z 354.2 [M+H]+

The synthetic route of 93668-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Antabio SAS; DAVIES, David; LEIRIS, Simon; (56 pag.)EP3572411; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem