Tag: M.W=100-200

Electric Literature of 149520-94-5, 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. 149520-94-5, name is Ethyl 2-amino-1H-imidazole-5-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Ethyl 2-amino-1H-imidazole-4-carboxylate (980 mg, 6.8 mmol) and tert- butyl 2-(2,4-dichloroben2ylidene)-3-oxobutanoate (2.03 g, 6.4 mmol) were dissolved in ethanol (15 mL) and the reaction was heated to 75 C for 16 h. The reaction was concentrated under reduced pressure to obtain a 10: 1 mixture (by EtaPLC) of 6-tert- butyl 2-ethyl 5-(2,4-dichlorophenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidine- 2,6-dicarboxylate and 6-tert~butyl 3-ethyl 5-(2,4-dichlorophenyl)-7-methyl-5,8- dihydroimidazo[1,2-a]pyrimidine-3,6-dicarboxylate (3.07 g, 100% crude yield) as a yellow foam. A small amount of this mixture (350 mg) was purified by silica gel chromatography to obtain 6-tert-butyl 2-ethyl 5-(2,4-dichlorophenyl)-7-methyl-5,8- dihydroimidazo[1,2-a]pyrimidine-2,6-dicarboxylate (190 mg, 54%) and 6-tert-butyl 3-ethyl 5-(2,4-dichlorophenyl)-7-methyl-5,8-diliydroimidazo[1,2-a]pyrimidine-3 ,6- dicarboxylate (19 mg, 5.4%) as white solids.[00249] For 2-isomer: 1H NMR (400 MHz, CDCl3) delta 10.19 (br s, 1H), 7.43 (d, J= 2.2 Hz, IH), 7.38 (s, 1H), 7.34 (d, J= 7.2 Hz, 1H), 7.21 (dd, J= 2.2, 7.2 Hz, 1H), 6.67 (s, 1H), 4.29 (m, 2H), 2.57 (s, 3H), 1.34 (t, J= 7.0 Hz, 3H), 1.26 (s, 9H).[00250] HPLC-MS Phenomenex LUNA C- 18 4.6 X 50 mm, 0 to 100% B over 4 minutes, 1 minutes hold time, A = 90% water, 10% methanol, 0.1% TFA, B = 10% water, 90% methanol, 0.1% TFA, RT = 4.13 rnin, 98% homogeneity index. [00251] LCMS: Anal. Calcd. for C21H23Cl2N3O4451.11 found: 452.24 (M+H)+. [00252] For 3-isomer: 1H NMR (400 MHz, CDCl3) delta 11.72 (br s, 1H), 7.59 (d, J= 8.4 Hz, 1H), 7.50 (br s, 1H), 7.27 (d, J= 3.5 Hz, 1H), 7.18 (dd, J= 3.0, 8.4 Hz, 1H), 6.91 (s, 1H), 4.16 (m, 2H), 2.44 (s, 3H), 1.41 (s, 9H), 1.26 (t, J= 7.0 Hz, 3H). [00253] HPLC-MS Phenomenex LUNA C-18 4.6 x 50 mm, 0 to 100% B over 4 minutes, 1 minutes hold time, A = 90% water, 10% methanol, 0.1% TFA, B = 10% water, 90% methanol, 0.1% TFA, RT = 4.24 min, 99% homogeneity index.[00254] LCMS: Anal. Calcd. for C21H23Cl2N3O4451.11 found: 452.24 (M+H)+. [00255] To a stirred solution of 6-tert-butyl 2-ethyl 5-(2,4-dichlorophenyl)-7- methyl-5,8-dmydroimidazo[1,2-a]pyrimidrne-2,6-dicarboxylate (191 mg, 0.42 mmol) in acetone (5 mL) was added KMnO4 (66 mg, 0.42 mmol). After 1 h, the reaction was filtered through celite and concentrated under reduced pressure. The resulting residue was diluted with CH2Cl2 and extracted with H2O (2x). The organic layer was dried EPO over MgSO4, concentrated under reduced pressure and recrystallized from EtOAc to obtain 6-tert-butyl 2-ethyl 5-(2,4-dicMorophenyl)-7-methylimidazo[1,2-a]pyrimidirie- 2,6-dicarboxylate (107 mg, 57%) as white crystals.[00256] To a stirred solution of 6-tert-butyl 3 -ethyl 5-(2,4-dichlorophenyl)-7- methyl-5,8-dihydroimidazo[l ,2-alpha]pyrimidine-3,6-dicarboxylate (19 mg, 0.04 mmol) in acetone (2 mL) was added KMnO4 (7 mg, 0.04 mmol). After 1 h, the reaction was filtered through celite and concentrated under reduced pressure. The resulting residue was diluted with CH2Cl2 and extracted with H2O (2x). The organic layer was dried over MgSO4, concentrated under reduced pressure and purified by silica gel chromatography to obtain 6-tert-butyl 3-ethyl 5-(2,4-dichlorophenyl)-7- methylimidazo[1,2-a]pyrimidine-2,6-dicarboxylate (14 mg, 74%) as white solid. [00257] For 2-isomer: 1H NMR (400 MHz, CDCl3) delta 7.68 (d, J= 1.8 Hz, 1H), 7.53 (s, 1H), 7.50 (dd, J= 1.8, 7.6 Hz, 1H), 7.35 (d, J= 7.6 Hz, 1H), 4.43 (m, 2H), 2.77 (s, 3H), 1.41 (t, J= 7.2 Hz, 3H), 1.29 (s, 9H). [00258] 13C NMR (500 MHz, CDCl3) 6 163.7, 162.7, 159.8, 147.0, 141.1, 138.5, 138.2, 134.5, 131.4, 130.3, 128.1, 127.8, 119.0, 114.1, 83.8, 61.4, 27.7, 24.3, 14.3. [00259] HPLC-MS Phenomenex LUNA C-18 4.6 X 50 mm, 0 to 100% B over 4 minutes, 1 minutes hold time, A = 90% water, 10% methanol, 0.1% TFA, B = 10% water, 90% methanol, 0.1% TFA, RT = 3.89 min, 99% homogeneity index. [00260] LCMS: Anal. Calcd. for C21H21Cl2N3O4449.09 found: 450.11 (M+H)+. [00261] HRMS: Anal. Calcd. for C21H22Cl2N3O4 450.0987 found: 450.0981 (M+H)+.[00262] For 3-isomer: 1H NMR (400 MHz, CDCl3) delta 8.38 (s, 1H), 7.41 (d, J= 1.7 Hz, 1H), 7.41 (m, 2H), 3.98-4.17 (m, 2H), 2.77 (s, 3H), 1.27 (s, 9H), 1.22 (t, J= 7.0 Hz, 3H).[00263] 13C NMR (400 MHz, CDCl3) delta 164.0, 159.1, 158.3, 150.5, 144.4, 142.4, 137.0, 134.8, 131.7, 129.9, 128.9, 126.9, 121.1, 117.6, 83.9, 61.0, 27.5, 23.5, 14.3. [00264] HPLC-MS Phenomenex LUNA C-18 4.6 x 50 mm, 0 to 100% B over 4 minutes, 1 minutes hold time, A = 90% water, 10% methanol, 0.1% TFA, B = 10% water, 90% methanol, 0.1% TFA, RT = 3.89 min, 99% homogeneity index.[00265] LCMS: Anal. Calcd. for C21H21Cl2N3O4449.09 found: 450.20 (M+H)+. EPO [00266] The regiochemistry for the 2- and 3-isomers were unequivocally established by single crystal X-ray analysis for both compounds.

The synthetic route of Ethyl 2-amino-1H-imidazole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/71752; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 66247-84-5, These common heterocyclic compound, 66247-84-5, name is (1H-Imidazol-4-yl)methanamine 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.

EXAMPLE 1 N-[(1H-Imidazol-4-yl)methyl]-1H-indole-3-carboxamide hydrochloride A suspension of indole-3-carboxylic acid (0.592 g) and thionyl chloride (0.6 ml) in 1,2-dichloroethane (50 ml) was stirred at room temperature for 60h under nitrogen. The suspension was evaporated in vacuo and further 1,2-dichloroethane (50 ml) was added. The suspension was re-evaporated to give a solid (0.6 g) which was dissolved in acetonitrile (25 ml) and triethylamine (5 ml), and added to a stirred suspension of imidazole-4-methanamine dihydrochloride (0.684 g) and triethylamine (5 ml) in acetonitrile (25 ml) at -5¡ã under nitrogen. The reaction was stirred for 1h while warming to room temperature and then heated at reflux for 20h. The mixture was evaporated in vacuo, dissolved in methanol (20 ml) and partitioned between hydrochloric acid (0.2N; 2*200 ml) and dichloromethane (2*100 ml). The combined aqueous layers were basified with saturated potassium carbonate and extracted with chloroform (3*150 ml). The combined chloroform layers were dried and evaporated in vacuo to give a semi-solid which was triturated with ether to give a solid (0.24 g). This was adsorbed onto silica and purified by FCC eluding with System A (83.5:151.5) to give a solid (ca. 50 mg) which was dissolved in methanol (3 ml) and acidified with ethanolic hydrogen chloride. Dry ether (20 ml) was added until the solution turned cloudy, precipitating the title compound (26 mg), m.p. 225¡ã-229¡ã (decomp.). Analysis Found: C,55.1; H,4.7; N,19.5; C13 H12 N4 O. HCl. 0.38H2 O requires C,55.1; H,4.5; N,19.5percent

Statistics shows that (1H-Imidazol-4-yl)methanamine hydrochloride is playing an increasingly important role. we look forward to future research findings about 66247-84-5.

Reference:
Patent; Glaxo Group Limited; US5026722; (1991); A;,
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 89088-69-7 as follows. Computed Properties of C4H8ClN3

Intermediate 22; 6-Chloro- 1 -methyl-iV-( 1 -methyl- lH-imidazol-4-yl)- lH-pyrazolo[3 ,4-Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; CHUAQUI, Claudio, Edmundo; HUANG, Shan; IOANNIDIS, Stephanos; SHI, Jie; SU, Mei; SU, Qibin; WO2010/38060; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 2080-75-3, 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. 2080-75-3, name is 5-Methoxy-1H-benzo[d]imidazol-2(3H)-one belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5.2 5-Methoxy-6-nitro-1H-benzo[d]imidazol-2(3H)-one (9) A solution of 17.5% fuming nitric acid (12.5 mL, 48.9 mmol) was slowly added to 5-methoxy-1H-benzo[d]imidazol-2(3H)-one (0.25 g, 1.5 mmol) at 0 C, and the reaction was stirred for 1 h at 0 C, and at 20 C for 3 h. The reaction mixture was cooled to 0 C and neutralised with saturated aqueous NaHCO3 solution. The product was extracted with EtOAc (2 * 50 mL), washed with water, dried, and concentrated to give 9 (113 mg, 36%) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) delta = 11.21 (br s, 1H), 10.81 (br s, 1H), 7.47 (s, 1H), 6.80 (s, 1H), 3.89 (s, 3H); MS ES+ve m/z 210 (M+H)+, 251 (M+H+MeCN)+.

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, 5-Methoxy-1H-benzo[d]imidazol-2(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Miah, Afjal H.; Abas, Hossay; Begg, Malcolm; Marsh, Benjamin J.; O’Flynn, Daniel E.; Ford, Alison J.; Percy, Jonathan M.; Procopiou, Panayiotis A.; Richards, Steve A.; Rumley, Sally-Anne; Bioorganic and Medicinal Chemistry; vol. 22; 15; (2014); p. 4298 – 4311;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 50591-22-5, These common heterocyclic compound, 50591-22-5, name is 1-Methyl-1H-benzo[d]imidazol-5-ol, 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 98 NaH (204 mg, 8.49 mmol) in 47 DMF (5 mL) was added 203 1-methyl-1H-benzo[d]imidazol-5-ol (420 mg, 2.83 mmol) at 28 C. After being stirred for 5 minutes, 41 ethyl 2-bromoacetate (568 mg, 3.4 mmol) was added and the resulting mixture stirred for a further 16 h under the reaction was complete by TLC. The mixture was treated with 43 water (50 mL) and extracted with ethyl acetate (2¡Á20 mL). The water layer was treated with 2N 44 HCl until pH 3 and extracted with ethyl acetate (2¡Á20 mL). The combined organic layers were washed with brine (30 mL), dried over Na2SO4 and concentrated to give the 205 product (160 mg, 24.1%) as white solid which was used in next step without further purification. LCMS (m/z): 207.1 (M+1).

The synthetic route of 50591-22-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Epizyme, Inc.; Duncan, Kenneth W.; Chesworth, Richard; Boriack-Sjodin, Paula Ann; Munchhof, Michael John; Jin, Lei; (118 pag.)US2019/83482; (2019); 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. 10394-39-5, name is 5-Methoxy-1-methyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C9H10N2O

To a solution of 5-methoxy-l-methyl-lH-benzo[d]imidazole (500 mg, 3.08 mmol) in CH2C12 (6 ml) was added BBr3 (3.1 g, 12.33 mmol) dropwise at 0C. After addition, the mixture was stirred for 2 h at 0C. The mixture was then quenched by slow addition to ice water (50 mL). The resulting mixture was extracted with CH2C12 (2×20 mL). The combined organic layers were washed with brine (30 mL), dried over Na2S04 and concentrated to give the title compound (100 mg, 21.9%) as a white solid which was used in next step without further purification. LCMS (m/z): 149.1 (M+l).

The synthetic route of 10394-39-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EPIZYME, INC.; DUNCAN, Kenneth, W.; CHESWORTH, Richard; BORIACK-SJODIN, Paula, Ann; MUNCHHOF, Michael, John; JIN, Lei; WO2014/100730; (2014); 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. 41270-74-0, name is 5-Phenyl-1H-imidazole-2-carboxylic acid, A new synthetic method of this compound is introduced below., Quality Control of 5-Phenyl-1H-imidazole-2-carboxylic acid

To a solution of intermediate 12-g (229 mg, 0.44 mmol) in DMF, cooled to 0¡ã C., were sequentially added 5-phenyl-1H-imidazole-2-carboxylic acid (195 mg, 0.87 mmol), HATU (220 mg, 0.57 mmol) and DIPEA (310 uL, 1.78 mmol) and the reaction mixture was stirred at 0¡ã C. for 1 hour. Saturated aqueous ammonium chloride and ethyl acetate were added; the organic layer was separated, washed with saturated aqueous ammonium chloride, saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by silica gel chromatography provided intermediate 60-a as a white foam.

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; Pharmascience Inc.; Laurent, Alain; Proulx, Melanie; Rose, Yannick; Denissova, Irina; Dairi, Kenza; Jarvis, Scott; Jaquith, James B.; (189 pag.)US9284350; (2016); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 154094-97-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 154094-97-0 name is 2-(1H-Imidazol-1-yl)ethanamine hydrochloride, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: At room temperature, to a red solution of compound 2 (150 mg,0.5 mmol) and triethylamine (0.14 mL, 1.0 mmol) in chloroform(40 mL), thionyl chloride (2.5 mL) was added dropwise. Themixture was stirred and heated under reflux for 5 h. The mixturegradually became a red solution. The reaction solution was then cooled to room temperature. The solvent was evaporated underreduced pressure. The residue was obtained under reduced pressurefor a period to get rid of most of the residual SOCl2 to give an orange solid residue. 4-(Dimethylamino)pyridine (70 mg,0.6 mmol) and different amine or alcohol derivative (1.80 mmol) inchloroform (30 mL) were added dropwise to the resultant residue.The reaction mixture instantaneously became a red solution. Thereaction mixture was heated under reflux for 5 h, and cooled toroom temperature. The solvent was evaporated under reducedpressure. The crude product was purified by silica gel columnchromatography to give the target compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(1H-Imidazol-1-yl)ethanamine hydrochloride, and friends who are interested can also refer to it.

Reference:
Article; Yu, Le-Mao; Zhang, Xiao-Ru; Li, Xiao-Bing; Yang, Yuan; Wei, Hong-Yu; He, Xi-Xin; Gu, Lian-Quan; Huang, Zhi-Shu; Pommier, Yves; An, Lin-Kun; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 525 – 533;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 30086-64-7,Some common heterocyclic compound, 30086-64-7, name is Hexahydro-1H-benzo[d]imidazole-2(3H)-thione, molecular formula is C7H12N2S, 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 alkyl chloroglyoxalates (5 mmol), cyclohexyl isocyanide (Cy-CN,5 mmol), and thiourea derivatives (5 mmol) was added to a mixture of GO-H2PO4(0.1 g) in acetonitrile for 2 h at 50 C. The catalyst was removed by filtration, and the solvent was evaporated to yield 4-hydroxy-thiazolidine-4-carboxylates. All products are solid and purified by recrystallization in ethanol.

The synthetic route of 30086-64-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Abdouss, Majid; Asadi, Elham; Daghlavi, Amneh; Ghasemi, Mohammad Hadi; Kowsari, Elaheh; Research on Chemical Intermediates; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 29518-68-1, 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. 29518-68-1, name is 2-(1H-Benzo[d]imidazol-2-yl)ethanamine belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Starting amino compound (0.238 mmol) was dissolved in THF (25 mL) and triethylamine (10 drops) was added to the stirred solution. Acyl halide (0.149 mmol) was added dropwise to the stirred solution, which was then heated under reflux for 3h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in EtOAc and washed with aq. K2CO3 solution followed by brine. The organic layer was then dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 1-5 methanol/DCM v/v.

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:
Article; Elshihawy, Hosam; Helal, Mohamed A.; Said, Mohamed; Hammad, Mohamed A.; Bioorganic and Medicinal Chemistry; vol. 22; 1; (2014); p. 550 – 558;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem