Author: Jessica.F

Application of 10394-38-4, 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 10394-38-4 as follows.

2.2 N-(1-Methyl-1H-benzimidazol-5-yl)-5-fluoro-1-[(pyrid-3-yl)methyl]-1H-indole-2-carboxamide hydrochloride (1:2) (Compound 4) 4.1 ml of trimethylaluminum (2M in toluene) are added under argon to a solution of 0.414 g (2.82 mmol) of 5-amino-1-methyl-1H-benzimidazole in 10 ml of dry toluene. After 15 minutes, 0.7 g (2.35 mmol) of ethyl 5-fluoro-1-[(pyrid-3-yl)methyl]-1H-indole-2-carboxylate, obtained in step 2.1, is added. The reaction medium is refluxed for 4 hours and then stirred overnight at room temperature. It is poured onto 100 g of ice and 50 ml of dichloromethane. A suspension is obtained, which is filtered and washed with water and ether. The residue is purified by preparative chromatography on alumina (eluent: dichloromethane/methanol). 0.36 g of a solid is obtained, which is dried under reduced pressure. The resulting solid is taken up in 30 ml of dichloromethane and 0.55 ml of a 4N solution of hydrogen chloride in dioxane is added. The solution is concentrated under reduced pressure and the resulting solid is recrystallized from a mixture of isopropanol and methanol. 0.36 g of the expected product is thus obtained in the form of a hydrochloride. Melting point (2HCl): 268-270 C. 1H NMR (DMSO D6), delta (ppm): 4.03 (s, 3H); 6 (s, 2H); 7.18 (dxd, 1H); 7.56 (dxd, 1H); 7.68 (m, 2H); 7.9 (m, 4H); 8.41 (s, 1H); 8.69 (m, 2H); 9.59 (s, 1H).

According to the analysis of related databases, 10394-38-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI-AVENTIS; US2008/146646; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 144689-93-0, These common heterocyclic compound, 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, 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 15 Ethyl 1-[(2′-t-butoxycarbonylbiphenyl-4-yl)methyl]-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate (Compound No. 1-119) Following a procedure similar to that described in Example 1(a), but using 0.845 g of ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate (prepared as described in Preparation 9) and 1.22 g of t-butyl 4′-bromomethylbiphenyl-2-carboxylate, 1.31 g of the title compound were obtained as a gum. This compound was allowed to stand at room temperature, which caused it to crystallize. It was then recrystallized from a mixture of diisopropyl ether and hexane, to give pure title compound, melting at 90-91 C. Nuclear Magnetic Resonance Spectrum (CDCl3) delta ppm: 0.97 (3H, triplet, J=7 Hz); 1.23 (3H, triplet, J=7 Hz); 1.25 (9H, singlet); 1.60 (6H, singlet); 1.82 (2H, sextet, J=7 Hz); 2.67 (2H, triplet, J=7 Hz); 4.24 (2H, quartet, J=7 Hz); 5.51 (2H, singlet); 5.72 (1H, singlet); 6.87-7.85 (8H, multiplet).

Statistics shows that Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate is playing an increasingly important role. we look forward to future research findings about 144689-93-0.

Reference:
Patent; Sankyo Company, Limited; US5616599; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 144690-33-5, The chemical industry reduces the impact on the environment during synthesis 144690-33-5, name is Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate, I believe this compound will play a more active role in future production and life.

In the equipped with electric stirrer, condenser and a thermometer of the 500 ml three-necked flask, add 20.00g (27.93mmol) intermediate I, 3.13g (55.87mmol) KOH and 80g acetone, for 55 C stirring for 3 hours (TLC monitoring), after the stop of the reaction, to cool down to 20 – 30 C, concentrated to no longer under the dripped, for 1M hydrochloric acid to adjust the pH=3, a large number of white solid precipitated, stirring at the room temperature 1 – 2h, filtering, the filter cake drying added 60 ml ethyl acetate at room temperature beating, filtering, the filter cake is dried to obtain the 11.50g impurities (see Figure 3) F, HPLC: 98.55%, yield: 59.77%.

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-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Tsingtao Yellow Sea Pharmaceutical Co., Ltd.; Liu Chuanfei; Chen Xiaotao; Li Yanshun; Wang Jiahui; Liu Ningning; Yang Kebao; (15 pag.)CN106831727; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, 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. Application In Synthesis of 1,1′-Sulfonyldiimidazole

General procedure: A solution of 500 mg (4.46 mmol) of 2-fluorophenol 1.769 g (8.92 mmol) of 1,1?-sulfonyldiimidazole in 15 mL of tetrahydrofuran was treated with 727 mg (2.23 mmol) of cesium carbonate. The reaction was stirred for 12 h, concentrated, and the residue was partitioned between the ethyl acetate and water (10 mL each). The organic layer was washed sequentially with saturated ammonium chloride solution and brine. After drying over the anhydrous sodium sulfate, the organic layer was concentrated and chromatographed on silica with 1:5 ethyl acetate / hexane as the eluant to afford 880 mg (90%) of 11bas a clear oil:

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

Reference:
Article; Yang, Baocheng; Sun, Zhexun; Liu, Changzhi; Cui, Yan; Guo, Zhilei; Ren, Yuwei; Lu, Zhijian; Knapp, Spencer; Tetrahedron Letters; vol. 55; 49; (2014); p. 6658 – 6661;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

15965-54-5, A common heterocyclic compound, 15965-54-5, name is 2-Chloro-5-methoxy-1H-benzo[d]imidazole, molecular formula is C8H7ClN2O, 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 33 2-Chloro-5-methoxy-1-(2,3-di-O-acetyl-5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole 2-Chloro-5-methoxy-1H-benzimidazole (0.661 g, 3.6 mmol) was coupled to 1,2,3-tri-O-acetyl-5deoxy-D-ribofuranose according to General Procedure II. The crude product was purified by flash chromatography (9:1 methylene chloride/ether) to yield the title compound (0.900 g, 65%) as a ~1:1 mix of regioisomers (1H NMR); MS (AP): m/z 405 (M+Na); 1H NMR (DMSO-d6) delta: 7.65-7.54 (two d, 1H), 7.21 (s, 1H), 6.97 (m, 1H), 6.18-6.11 (two d, 1H), 5.70-5.59 (m, 1H), 5.21 (q, 1H), 4.27 (m, 1H), 3.83 (two s, 3H), 2.16 (s, 3H), 2.05 (s, 3H), 1.51 (t, 3H).

The synthetic route of 15965-54-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Regents of the University of Michigan; Glaxo Wellcome Inc.; US6413938; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 864076-05-1, These common heterocyclic compound, 864076-05-1, name is Methyl 4-bromo-1-methyl-1H-imidazole-2-carboxylate, 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.

A solution of (3^)-3-hydroxy-l-methyl-3-[2-[3-(4,4,5,5-tetramethyl-l ,3,2- dioxaborolan-2-yl)phenyl]ethynyl]pyrrolidin-2-one (73 mg., 0.21 mmol), methyl 4-bromo-l- methyl-lh-imidazole-2-carboxylate (40 mg, 0.18 mmol), cesium fluoride (54 mg, 0.36 mmol) and bis(triphenylphosphine)palladium(II) dichloride (12.5 mg, 0.018 mmol) in ethanol (1.5 mL) and water (1.0 mL) was degassed. The reaction mixture was heated in microwave at 100 °C for 45 min. The reaction was filtered through celite. The crude product was purified by flash chromatography (MeOH/DCM) then submitted for rHPLC to give product (27 mg, 42.7percent). LC-MS (ES, m/z): 354 [M+H]+.

The synthetic route of 864076-05-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; CASTANEDO, Georgette; FENG, Jianwen A.; CRAWFORD, James John; LEE, Wendy; LIN, Xingyu; HU, Baihua; WU, Guosheng; (218 pag.)WO2016/135163; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 68282-53-1, A common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, 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.

COMPOUND 12.1. 60: N*N-DIETHYL-4-f6-METHOXY-2-r (5-METHYL-1H- IMIDAZOL-4-YL) METHYLI-7- (NEOPENTYLOXY-1, 2, 3, 4- TETRAHYDROISOOUINOLIN-1-YUBENZAMIDE; To a solution of INTERMEDIATE 7.1. 4 (18 mg, 0.0424 mmol), 4-methyl-1H- imidazole-5-carboxaldehyde (5.8 mg, 0.052 mmol, 1. 2eq) in 1,2-dichloroethane (2 mL) was added sodium triacetoxyborohydride (11.1 mg, 0.052 mmol). The reaction mixture was stirred at room temperature for overnight, then diluted with dichloromethane (5 mL), quenched with saturated aqueous sodium bicarbonate (0.5 mL) and separated. The organic phase was washed with brine (1 x 2 mL), dried (MgSO4) and filtered. To the filtrate ps-scavenger was added, stirred for 2hr and filtered. The filtrate was concentrated and purified by flash chromatography to give compound COMPOUND 12.1. 60 (15 mg, 0.0029 mmol, 68%) as colorless oil. lHNMR (500 MHz, CD2Cl2) : No. 0. 89 (s, 9H), 1.00 (br s, 3H), 1.24 (br s, 3H), 1.90 (s, 3H), 1.99 (s, 2H), 2.45 (m, 1H), 2.68 (m, 1H), 2. 82 (m, 2H), 3.15 (br s, 2H), 3.28 (m, 2H), 3.40 (br s, 2H), 3.70 (s, 3H), 4.45 (s, 1H), 6.10 (br s, 1H), 6.51 (s, 1H), 7.29-7. 33 (m, 4H), 8.18 (s, 1H). (+) LRESIMS m/z 519 [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; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 35203-44-2,Some common heterocyclic compound, 35203-44-2, name is 1-Propyl-1H-imidazole, molecular formula is C6H10N2, 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.

A 100-mL two-neck flask was placed, N-propylimidazole (2.10 g, 18.0 mmol) and 35 mL of toluene were added, and 3-bromopropyldiethoxyphosphine oxide (5.18 g, 20.0 mmol) was added dropwise with heating and stirring.And reacted at 85 °C for 6 h and cooled to room temperature. Pour out the upper toluene,100 mL of deionized water was added to dissolve the product to obtain an aqueous phase. The aqueous phase was washed with an EtOAc_PE=3:1 organic phase (30 mL×4) to separate the aqueous phase II; di(2-ethylhexyl) phosphate (P204). ) (5.80 g, 18.0 mmol) was refluxed under the action of sodium for 24 h. The resulting sodium salt was dissolved in methylene chloride and the separated aqueous phase was stirred at room temperature for 3 h.Add 50 mL of CH2Cl2 and stir to separate the organic phase. The organic phase was washed with deionized water (20 mL×5) and the organic phase was obtained after liquid separation. The organic phase was dried by adding anhydrous Na 2 SO 4 , filtered, and most of the CH 2 Cl 2 was evaporated under reduced pressure and dried in vacuum at 70° C. for 3 h. Yellow sticky liquid product 9.45g (yield 86percent),

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

Reference:
Patent; Ningbo University; Wang Junping; Liang Hongze; Feng Da; Zhao Jieying; Kang Xinchun; Zhang Xiaozhen; Shen Fei; Huang Feilong; (21 pag.)CN104945435; (2018); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 2620-76-0, These common heterocyclic compound, 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, 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.

(1-7) Synthesis of Compound (1); Into a 300 ml three-necked flask, 2.0 g (5.0 mmole) of Intermediate 6, 3.9 g (11 mmole) of 2-(4-bromophenyl)-1-phenylbenzimidazole, 0.23 g (0.20 mmole) of tetrakis(triphenylphosphine)palladium(0), 50 ml of 1,2-dimethoxyethane and 15 ml (30 mmole) of a 2 M aqueous solution of sodium carbonate were placed under the stream of argon, and the resultant mixture was heated under the refluxing condition for 8 hours. After the reaction was completed, the organic layer was washed with water and dried with magnesium sulfate, and the solvent was removed by distillation using a rotary evaporator. The obtained crude crystals were washed with 50 ml of toluene and 100 ml of methanol, and 3.4 g of a light yellow powder substance was obtained. The obtained substance was identified to be Compound (1) by the measurement of the field desorption mass spectrum (FD-MS) (the yield: 80percent).

The synthetic route of 2620-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; US8058450; (2011); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1615-14-1,Some common heterocyclic compound, 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, molecular formula is C5H8N2O, 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.

Diethyl azodicarboxylate (435 mg, 2.5 mmol) was added dropwise to a suspension of 7-hydroxy-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin4-one (612 mg, 2 mmol), 2-(imidazol-1-yl)ethanol (280 mg, 2.5 mmol), (J. Med. Chem. 1993, 25 4052-4060), and triphenylphosphine (655 mg, 2.5 mmol) in methylene chloride (10 ml) at 5 C. The mixture was stirred for 10 minutes at 5 C. and then 1 hour at ambient temperature. The mixture was poured directly on to a silica column and eluted with methylene chloride/methanol (95/5) to give 7-(2-(imidazol-1-yl)ethoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (640 mg, 80%). 1H NMR Spectrum: (CDCl3) 1.19(s, 9H); 3.98(s, 3H); 4.34(m, 2H); 4.45(m, 2H); 5.94(s, 1H); 7.02(s, 1H); 7.07(s, 1H); 7.11(s, 1H); 7.64(s, 1H); 7.67(s, 1H); 8.17(s, 1H). MS-ESI: 423 [MNa]+

The synthetic route of 1615-14-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zeneca Limited; US6265411; (2001); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem