Tag: M.W=100-200

Reference of 124312-73-8,Some common heterocyclic compound, 124312-73-8, name is (1-Methyl-1H-imidazol-2-yl)methanamine, molecular formula is C5H9N3, 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.

The compound (225 mg) obtained in Example 55-3 was dissolved in methanol (4.0 ml). The solution was added with the compound (64.5 mg) obtained in Example 14-7 and trimethyl orthoformate (0.13 ml) and the whole was stirred at room temperature for 1.5 hours. After having been cooled to 0C, the reaction solution was added with sodium borohydride (20.8 mg) and the whole was stirred at room temperature for 20 minutes. After the reaction solution was concentrated under reduced pressure, the resultant residue was added with distilled water and the whole was subjected to extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with an anhydrous sodium sulfate. The drying agent was filtrated out and then the organic layer was concentrated under reduced pressure. The resultant was dissolved in methanol (6.0 ml). The reaction solution was added with 2-imidazole carboxaldehyde (83.3 mg) and sodium cyanoborohydride (77.3 mg). The whole was added with acetic acid to adjust the pH to 5 and stirred at room temperature for 18 hours. The reaction solution was concentrated under reduced pressure. The resultant residue was added with a 1 mol/l sodium hydroxide aqueous solution and the whole was subjected to extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. The drying agent was filtrated out and then the organic layer was concentrated under reduced pressure. The resultant residue was purified through silica gel column chromatography (hexane/ethyl acetate) and treated with hydrochloric acid, thereby obtaining a hydrochloride (174.3 mg) of the subject compound as a white solid. MS(FAB,Pos.):m/z=567[M+H]+ 1H-NMR(500MHz,DMSO-d6):delta=0.90(6H,t,J=7.3Hz),1.64-1.86(8H,m),2.95(4H,br),3.05(2H,br),3.28(2H,br),3.67(3H,s),3.83(2H,s),4.10(2H,s),4.17(2H,s),5.94(2H,s),7.31-7.39(5H,m),7.49-7.54(3H,m),7.60(2H,s),7.72(1H,d,J=8.4Hz),8.17(1H,s),10.43(1H,br),14.94(2H,br).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (1-Methyl-1H-imidazol-2-yl)methanamine, its application will become more common.

Reference:
Patent; Kureha Corporation; EP1724263; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, 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 137049-00-4, category: imidazoles-derivatives

3-Isopropyl-2-oxo-2,3-dihydrobenzoimidazole-1-carboxylic acid [(1S,3R,5R)-8-((S)-2-hydroxy-3-methylaminopropyl)-8-azabicyclo[3.2.1]oct-3-yl]amide TFA salt, (prepared as described in Example 12, step (f)), (0.050 g, 0.078 mmol) was suspended in dimethylformamide (5 mL) and cooled to 0 C. N,N-diisopropylethylamine (0.43 mL, 24.6 mmol) was added, followed by 1-methyl-1-H-imidazole sulfonyl chloride (0.017 g, 0.094 mmol). The reaction was allowed to reach room temperature and was judged to be complete after about 1 hr. The reaction was quenched with acetic acid and water (1:1). Volatiles were removed and purification via prep HPLC (reverse phase) was accomplished on a gradient of 15-45% over 50 min; flow rate 20 mL/min, to provide the title compound (0.030 g, 56%) as a TFA salt. (m/z): [M+H]+ calcd for C26H37N7O5S 560.27; found 560.5. Retention time (anal. HPLC: 2-50% MeCN/H2O over 4 min)=4.05 min. 1H NMR (d6-DMSO): 9.28 (d, 1H), 8.08 (d, 1H), 7.79 (d, 2H), 7.45 (d, 1H), 7.21 (m, 2H), 4.75 (br m, 2H), 4.01 (m, 1H), 3.71 (br s, 4H), 3.23 (m, 3H), 2.88 (m, 1H), 2.77 (s, 2H), 2.29 (m, 2H), 2.08 (m, 2H), 1.93 (m, 4H), 1.59 (m, 2H), 1.48 (d, 6H).

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-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Theravance, Inc.; US2006/276482; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 20485-43-2,Some common heterocyclic compound, 20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid, molecular formula is C5H6N2O2, 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: A mixture of 1-methyl-1H-imidazole-2-carboxylic acid (0.130 g,1mmol), EDC.HCl (0.29 g, 1.5mM), HOBt (0.20 g, 1.5mmol) and Et3N(0.15 g, 1.5 mM) in dichloromethane (10 mL) was stirred for 1 h at 0 C. Then, L-phenylalanine methyl ester.HCl (1.05 mM) was added into the solution. The reaction mixture was stirred for 12 h at 25 Cand then evaporated to dryness. The ester obtained was washed with water and extracted with dichloromethane (Scheme 1). To a solutionof the ester (1 equiv) in a dichloromethane/methanol (9:1 v/v)mixture, was added a methanolic solution of NaOH (3 equiv) withfinal concentration of the alkali being about 0.1-0.2 N. The reaction was monitored by TLC for the disappearance of starting ester. After the completion of the reaction, the solvents were removed under vacuum and the residue was diluted with water. Then, the aqueous phase was acidified to pH 2-3 with dilute HCl and extracted with ethyl acetate. The combined organic layers were dried with anhydrous sodium sulfate (Na2SO4) and the solvent was removed to afford the acid (PAIC). Single crystal of PAIC was isolated by slow evaporation of the solvent. Yield: 143 mg (74%), M.P- 129 C; Anal.Calc. for C14H15N3O3: C, 61.53; H, 5.53; N, 15.38. Found C, 61.13; H,5.45; N,15.18; 1H NMR (DMSO-d6, 400MHz): delta/ppm3.16 (d, J 4Hz,2H, CH2), 3.8 (s, 3H, NeCH3), 4.6 (m, H, chiral H), 6.9e7.2 (m, 7H,Aromatic H), 8.2 (d, J 8.4 Hz, 1H, amide-NH); 13C NMR: 34.9 (CH3),36.2 (eCH2), 52.9 (CeNH), 158.5 (COeN), 172(eCOO); FT-IR (KBr, cm-1)1555 (NeH), 1602 (eC]N), 3292 (HOeCO), 1673 (C]Oamide), 2931 (CeH); ESI mass: m/z 272.9.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-imidazole-2-carboxylic acid, its application will become more common.

Reference:
Article; Annaraj; Mitu; Neelakantan; Journal of Molecular Structure; vol. 1104; (2016); p. 1 – 6;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 36947-68-9, A common heterocyclic compound, 36947-68-9, name is 2-Isopropyl-1H-imidazole, molecular formula is C6H10N2, 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-isopropyl-lH-imidazole (155 mg) in N,N-dimethylformamide (4 ml), was added NaH (56.4 mg) portionwise. After stirring for 15 min at room temperature, 5-fluoro- 2-nitroaniline61 (200 mg) was added and the reaction mixture was heated at 60 C for 16 hours. The reaction mixture was diluted with ethyl acetate and washed with aq. sodium bicarbonate. The organic layer was dried over MgS04, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, eluent: 0 to 5% of methanol in dichloromethane) to afford 5-(2-isopropyl-lH-imidazol-l-yl)-2-nitroaniline (85mg, 27%) as an orange solid. MS (ISP): 247.2 ([M+H]+).

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GOERGLER, Annick; NORCROSS, Roger; DEY, Fabian; KUSZNIR, Eric Andre; (206 pag.)WO2019/43217; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 16042-25-4, These common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, 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.

lH-Imidazole-2-carboxylic acid (100 mg, 0.892 mmol), 1,4- dichloro-2-(chloromethyl)benzene (382 mg, 1.96 mmol), and K2C03 (370 mg, 2.68 mmol) were combined in DMF. The suspension was stirred at 100 C for 1 h, then added to 5% aqueous HC1 and extracted with EtOAc. The organic phase was washed with saturated aqueous NaHC03, H20, and brine, then dried over Na2S04 and the solvent removed under reduced pressure. The crude residue was purified by flash- column chromatography using a gradient of DCM : MeOH (100 : 0 to 98 : 2) to give 62a (290 mg, 76%) as a yellow oil.

Statistics shows that 2-Imidazolecarboxylic acid is playing an increasingly important role. we look forward to future research findings about 16042-25-4.

Reference:
Patent; ARDELYX, INC.; LEWIS, Jason, G.; REICH, Nicholas; CHEN, Tao; JACOBS, Jeffrey W.; CHARMOT, Dominique; NAVRE, Marc; FINN, Patricia; CARRERAS, Christopher; SPENCER, Andrew; WO2013/96771; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, 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 1003-21-0, name: 5-Bromo-1-methyl-1H-imidazole

[0206] A solution of isopropylmagnesium chloride/lithium chloride complex (1.3 M in THF, 19.5 mE, 25.35 mmol) was added dropwise by syringe to a solution of 5-bromo-1-me- thyl-1H-imidazole (4.12 g, 25.58 mmol) in dry THF (130 mE) at 0 C. After 15 minutes, the Grignard solution was added via cannulation to a solution of picolinaldehyde (2.0 ml, 20.93 mmol) in dry THF (55 mE) at 0 C. The reaction mixture was stirred for 5 minutes at 0 C., then warmed to room temperature for 1 hour. The reaction mixture was then cooled in an ice bath and quenched with saturated aqueous ammonium chloride. The mixture was partitioned between brine and ethyl acetate. The separated aqueous phase was further extracted with ethyl acetate. The organic phase was dried (Na2504), filtered, and concentrated. The crude product was purified by flash column chromatography (silica gel, 0-5% MeOH-DCM) to provide the title compound as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1-methyl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Cummings, Maxwell D.; US2015/105365; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 131020-36-5, A common heterocyclic compound, 131020-36-5, name is Methyl 1-methyl-1H-benzo[d]imidazole-5-carboxylate, molecular formula is C10H10N2O2, 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.

Preparation of ( 1 -methyl- l H-benzimidazol- – l methanolThe title compound was synthesized by esterification of l//-benzimidazole-5-carboxylic acid using methanol in presence of cone, sulphuric acid followed by N-methylation using methyl iodide in presence of potassium carbonate and subsequent reduction of the ester group by lithium aluminium hydride; NMR (300 MHz, DMSO- 6) delta 3.84 (s, 3H), 4.59 (s, 2H), 5.23 (br s, l H), 7.26 (d, J = 8.4 Hz, 1H), 7.52-7.58 (m, 2H), 8.23-8.31 (m, 1 H).

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; GLENMARK PHARMACEUTICALS S.A.; LINGAM, Prasada, Rao, V., S.; THOMAS, Abraham; KHAIRATKAR-JOSHI, Neelima; BAJPAI, Malini; GULLAPALLI, Srinivas; DAHALE, Dnyaneshwar, Harishchandra; MINDHE, Ajit, Shankar; RATHI, Vijay, Eknath; WO2011/138657; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 4887-88-1, A common heterocyclic compound, 4887-88-1, name is 5-Bromo-1H-benzo[d]imidazole, molecular formula is C7H5BrN2, 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 crude, impure 5-bromobenzimidazole (46.2 g) and methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate (Synthesis, 1984, 10, 847-850) (42 g, 220 mmol) in 800 mL of CHCl3 was added N-methylimidazole (28 mL, 345 mmol). After 16 h, N-methylimidazole (17 mL, 220 mmol) and tert-butylchlorodimethylsilane (36 g, 240 mmol) was added. When TLC showed the reaction to be complete, the solution was diluted with water. The layers were separated. The organic phase was washed with water, dried over MgSO4 and concentrated onto celite. The crude mixture was purified by flash column chromatography (0-25% EtOAc:hexanes) in batches to separate the 2 regioisomers, giving 33.5 g of Intermediate 3 eluting first and 29.2 g of Intermediate 4 eluting second (58%). (Intermediate 3, 5-Br) 1H NMR (400 MHz, d6-DMSO) delta 8.77 (s, 1H), 8.01 (d, J=1.6 Hz, 1H), 7.76 (d, J=8.8 Hz, 1H), 7.56 (dd, J=8.8 and 1.6 Hz, 1H), 7.25 (s, 1H), 3.76 (s, 3H), 0.99 (s, 9H), 0.27 (s, 6H). (Intermediate 4, 6-Br) 1H NMR (400 MHz, d6-DMSO) delta 8.71 (s, 1H), 7.88 (d, J=1.6 Hz, 1H), 7.73 (d, J=8.8 Hz, 1H), 7.50 (dd, J=8.8 and 2.0 Hz, 1H), 7.26 (s, 1H), 3.77 (s, 3H), 0.99 (s, 9H), 0.26 (s, 6H).

The synthetic route of 4887-88-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kuntz, Kevin Wayne; Emerson, Holly Kathleen; Cheung, Mui; Badiang, Jennifer Gabriel; US2009/326029; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 3034-38-6, 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. 3034-38-6, name is 5-Nitro-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 268a 1-Methyl-4-nitro-1H-imidazole 268a To a mixture of 4-nitro-1H-imidazole (2.0 g, 17.7 mmol) and K2CO3 (3.67 g, 26.5 mmol) in acetonitrile (20 mL) was added iodomethane (1.3 mL, 3.0 g, 21.2 mmol) dropwise while stirring at room temperature. The resulting mixture was stirred at 60C overnight. It was then evaporated under reduced pressure and the residue was diluted with water (20 mL). The mixture was extracted with dichloromethane (2 X 20 mL). The combined extract was concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with 100:1 dichloromethane/methanol to afford 268a as a yellow solid (1.8 g, 82%). MS-ESI: [M+H]+ 128.1. 1H NMR (500 MHz, DMSO-d6) delta 8.37 (s, 1H), 7.82 (s, 1H), 3.76 (s, 3H).

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

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 13570-08-6, The chemical industry reduces the impact on the environment during synthesis 13570-08-6, name is 2-(1H-Benzo[d]imidazol-2-yl)acetic acid, I believe this compound will play a more active role in future production and life.

Thionyl dichloride (0.7 ml, 9.65 mmol) was added dropwise to an ice-cooled (0C) suspension of 2-(1H-1,3- benzodiazol-2-yl)acetic acid (179) (0.7 g, 3.97 mmol) in MeOH (30 ml). The reaction mixture was allowed to warm to room temperature and stirred for 18 h. The mixture was poured onto saturated NaHCQ (40 ml) and extracted with DCM (3 x 20 ml). The combined organic layers were washed with brine (30 ml), dried (NaS04), filtered and evaporated to give the title compound (0.65 g, 86%) as a cream solid. 1H-NMR(CDCI3, 500 MHz): d[ppm]= 10.10 (brs, 1H), 7.72 (brs, 1H), 7.46 (brs, 1H), 7.29-7.23 (m, 2H), 4.09 (s, 2H), 3.82 (s, 3H) HPLCMS (Method F): [m/z]: 191.2 [M+Hf

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, 2-(1H-Benzo[d]imidazol-2-yl)acetic acid, other downstream synthetic routes, hurry up and to see.

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