Tag: M.W=100-200

Electric Literature of 3314-30-5, A common heterocyclic compound, 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, molecular formula is C8H6N2O, 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: A suspension of methyl 2-(2-aminoethyl)-1 ,3-thiazole-4-carboxylate (5) (1.96 g, 10.52 mmol), 1 H- benzimidazole-2-carbaldehyde (2.31 g, 15.79 mmol) and DIPEA (1.83 ml, 10.52 mmol) in MeOH (100 ml) was stirred at room temperature for 12 h. The reaction mixture was cooled to 0¡ãC, NaBH4 (0.597 g, 15.79 mmol) was added and the mixture stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and the residue dissolved in EtOAc (100 ml) and washed with saturated NC03 (2 x 50 ml). The combined aqueous layers were extracted with EtOAc (3 x 50 ml) and the combined organic layers dried (MgS04), filtered and evaporated in vacuo. Purification by flash column chromatography (KP- NH, eluting with a gradient of 0-10percent MeOH / DCM) afforded the title compound (1.4 g, 38percent, 90percent purity) as a tan solid. 1 H-NMR (Methanol-d4, 250 MHz): d[ppm]= 8.27 (s, 1 H), 7.60 – 7.49 (m, 2H), 7.29 – 7.17 (m, 2H), 4.09 (s, 2H), 3.92 (s, 3H), 3.26 (t, J = 6.3 Hz, 2H), 3.10 (t, J = 6.8 Hz, 2H) HPLCMS (Method A): [m/z]: 317 [M+H]+In a similar fashion to general procedure 3, -(2-aminoethyl)-N’-[(3-fluoropyridin-2- yl)methyl]propanediamide (418) (190 mg , 0.75 mmol), 1 H-1 ,3-benzodiazole-2-carbaldehyde (120 mg, 0.82 mmol) and MgS04 (100 mg) in DCM (10 ml) and MeOH (5 ml) at room temperature for 16 h, followed by addition of NaBH4 (57 mg , 1 .51 mmol) gave the title compound (87 mg, 28percent) as a pale yellow solid after purification by basic prep-HPLC. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.14 (s, 1 H), 8.59 (t, J = 5.5 Hz, 1 H), 8.40 – 8.35 (m, 1 H), 8.06 (t, J = 5.5 Hz, 1 H), 7.69 (m, 1 H), 7.57 – 7.47 (m, 1 H), 7.47 – 7.36 (m, 2H), 7.16 – 7.08 (m, 2H), 4.48 (dd, J = 5.5, 1 .7 Hz, 2H), 3.91 (s, 2H), 3.20 (dt, J = 6.5, 6.5 Hz, 2H), 3.13 (s, 2H),2.63 (t, J = 6.5 Hz, 2H) HPLCMS (Method C): [m/z]: 385.2 [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; 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

Synthetic Route of 68282-53-1, 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. 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 8 SYNTHESIS OF 4-(3-CHLORO-4-FLUORO-PHENYLAMINO)-5-(5-METHYL-3H-IMIDAZOL4-YLMETHYLENE)-5,7-DIHYDRO-PYRROLO [2,3-D]PYRIMIDIN-6-ONE (FORMULA 8) 4-Chloro-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (1 eq.) was condensed with 5-methyl-3H-imidazole-4-carbaldehyde (1 eq.) at room temperature to give (76.9%) of 4-chloro-5-(5-methyl-3H-imidazol-4-ylmethylene)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one.

The synthetic route of 5-Methyl-1H-imidazole-4-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Liang, Congxin; Sun, Li; Wei, Chung Chen; Tang, Peng Cho; McMahon, Gerald; Hirth, Klaus Peter; Cui, Jingrong; US2002/183319; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 570-22-9, These common heterocyclic compound, 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic 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.

General procedure: A mixture of CoCl2¡¤6H2O (0.1 mmol, 0.0237 g), imidazole-4,5-dicarboxylate (0.1 mmol,0.0156 g), 1,4-bis(1-imidazoly)benzene (0.1 mmol, 0.0210 g), NaOH (0.2 mmol, 0.0800 g), H2O(10 mL) and DMF (2 mL) was stirred for 1 h in air, then transferred to and sealed in a 25 mLTeflon-lined reactor and heated in an oven to 110 C for 72 h. After cooling to room temperature,brown block crystals of 1 were collected by ltration and washed with water and DMFseveral times.

Statistics shows that 1H-Imidazole-4,5-dicarboxylic acid is playing an increasingly important role. we look forward to future research findings about 570-22-9.

Reference:
Article; Wang, Ke-Hua; Journal of Coordination Chemistry; vol. 70; 24; (2017); p. 3982 – 3995;,
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 1003-21-0 as follows. Recommanded Product: 5-Bromo-1-methyl-1H-imidazole

To a solution of 153.3 (2.5g, O.76mmol, 1.Oeq) and5-bromo-1-methyl-1H-imidazole (1.5g, O.92mmol, 1.2eq) in a mixture of 1,2-dimethoxyethane (2OmL) and water (5mL), sodium carbonate (2.4g, 2.3mmol, 3.Oeq) was added. Reaction mixturewas degassed with argon for 15mm. Then [1,1?-Bi s(diphenylphosphino)ferrocene]di chloropalladium(II) complex with CH2C12 (0. 9g, 0. O7mmol, O.leq) was added and again degassed for 5mm. Reaction mixture was stirred at 115 C for 2h. After completion of the reaction, the reaction mixture was transferred into water and extracted with ethyl acetate. Organic layers were combined, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to obtain crude product. This was purified by column chromatography using 2% MeOH in CH2C12 to obtain pure 212.1 (1.3g, 60.50%). MS(ES): m/z 281.57 [M+H].

According to the analysis of related databases, 1003-21-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NIMBUS LAKSHMI, INC.; GREENWOOD, Jeremy Robert; LEIT DE MORADEI, Silvana Marcel; MASSE, Craig E.; MCLEAN, Thomas H.; MONDAL, Sayan; (869 pag.)WO2018/75937; (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. 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 137049-00-4

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, 1 H) 7.84 (d, J=1.36 Hz, 1 H) 7.75 – 7.78 (m, 2 H) 7.48 (dd, J=9.49, 2.71 Hz, 1 H) 7.25 – 7.35 (m, 2 H) 7.21 (d, J=2.71 Hz, 1 H) 7.09 (dd, J=8.82, 2.71 Hz, 1 H) 7.03 (t, J=7.46 Hz, 1 H) 6.89 (d, J=8.82 Hz, 1 H) 6.83 (d, J=7.80 Hz, 2 H) 6.37 (d, J=9.49 Hz, 1 H) 3.67 (s, 3 H) 3.43 (s, 3 H). MS (ESI+) m/z 437 (M+H)+.

The synthetic route of 137049-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI)COMPANY, LTD.; HUBBARD, Robert Dale; MCDANIEL, Keith F.; PARK, Chang Hoon; PRATT, John K.; SOLTWEDEL, Todd; SUN, Chaohong; WANG, Le; WENDT, Michael D; WO2013/185284; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 6478-73-5, These common heterocyclic compound, 6478-73-5, name is 5,6-Dichloro-1H-benzo[d]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.

Example 23[0164] Preparation of (4aR, 7R, 8S,8aR) 5, 6-dichloro-1- (8-fluoro-2-phenyl-hexahydro- pyrano [3,2-d] [1,3]dioxin-7-yl)-1 H-benzoimidazole. EMI54.1[0165] To a solution of (4aR, 7S, 8R, 8aR) trifluoromethanesulfonic acid 8-fluoro-2- phenyl-hexahydropyrano [3,2-d] [1, 3] dioxin-7-yl ester (47.2 mg, 0.12 mmol), prepared according to earlier procedures, in 5 mL of DMSO was added 5, 6-dichloro-1H- benzoimidazole (524 mg, 2.8 mmol) and NaH (67 mg, 2.8 mmol). The mixture was stirred at 70 C overnight. After aqueous work-up and extraction with Et2O, The combined organic fractions were washed with brine, dried over Na2S04, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography to give (4aR, 7R, 8S, 8aR) 5, 6-dichloro-1- (8-fluoro-2-phenyl-hexahydro-pyrano [3,2-d] [1,3] dioxin- 7-yl)-1 H-benzoimidazole. [0166] Yield: 29. 4 mg (58%); Rf= 0. 5 (1: 1 EtOAc-hexane). 1H NMR (CDCl3, 300 MHz) 6 3.61-3. 75 (1H, ddd), 3.80 (1H, dt), 4.14 (1H, m), 4.44-4. 51 (3H, m), 4.66 (1H, m), 5.05-5. 21 (1H, d), 5.49 (1H, s), 7.26-7. 44 (5H, m), 7.60 (1H, s), 7.97 (1H, s), 8.51 (1H, s).

Statistics shows that 5,6-Dichloro-1H-benzo[d]imidazole is playing an increasingly important role. we look forward to future research findings about 6478-73-5.

Reference:
Patent; AUSPEX PHARMACEUTICALS, INC.; WO2005/49582; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 51-17-2, A common heterocyclic compound, 51-17-2, name is 1H-Benzo[d]imidazole, molecular formula is C7H6N2, 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) Put 30 g of water into the reaction kettle, turn on the stirring, and sequentially add 0.06 g of Fe (NO3) 3.9H2O, 15 g of 96% sulfuric acid, 0.03 g of tetrabutylamine bromide, 2.5 g of benzimidazole, and raise the temperature;(2) When the reaction temperature reaches 80 C, 20 g of oxone is added in batches, and the reaction is incubated for 8 hours after the addition.(3) After the reaction is completed, the temperature is lowered to -10 to 10 C, and concentrated ammonia is slowly added dropwise under stirring to adjust the pH value to 0.6 to 1, and then stirring is continued for 1 hour for crystallization, suction filtration, and drying to obtain 4,5-imidazole di Carboxylic acid, the filtrate can be used for further product recovery, yield 73%.

The synthetic route of 51-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Changshu Institute of Technology; Yang Yang; Fu Renzhong; Wang Xin; Fang Zhengjiao; Lu Zhengyi; Zeng Xiaojun; (11 pag.)CN110818628; (2020); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 10364-94-0, These common heterocyclic compound, 10364-94-0, name is (1H-Imidazol-1-yl)(phenyl)methanone, 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: In a round bottomed flask 0.01 mol (1.36 g) phenyl acetic acid and 0.012 mol (1.94 g) of CDI were added. The reaction mixture was mixed and grinded with a spatula. CO2 gas starts releasing with increase in temperature and solid reaction mixture was turned to pale yellow liquid within 5 min. 0.001 mol (0.1 g) Imidazole. hydrochloride, 0.01 mol (0.87 g) of morpholine, and 1 mL of water were added to it. The reaction mixture was kept at room temperature for another 10 min. Dilute hydrochloride solution was added to it and the aqueous layer was washed with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and concentrated to give pure product.

Statistics shows that (1H-Imidazol-1-yl)(phenyl)methanone is playing an increasingly important role. we look forward to future research findings about 10364-94-0.

Reference:
Article; Verma, Sanjeev K.; Ghorpade, Ramarao; Pratap, Ajay; Kaushik; Tetrahedron Letters; vol. 53; 19; (2012); p. 2373 – 2376;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1467-16-9, name is 1H-Imidazole hydrochloride, 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 1467-16-9, Product Details of 1467-16-9

A mixture of lithium(1+) ion 3-amino-7-bromo-5/-/-pyrrolo[2,3- 5]pyrazine-2-carboxylate, Intermediate 163 (243 mg, 0.924 mmol), CDI (300 mg, 1.85 mmol) and imidazole hydrochloride (116 mg, 1.11 mmol) in DMF (3 ml) was stirred at RT for 1 h 15 min. Additional CDI (100 mg, 0.617 mmol) was added then the reaction was left to stir at RT for a further 1 h. The reaction mixture was diluted with water (5 ml) then stirred at RT for 10 min. The resultant suspension was filtered then the collected solid was washed with water (2 x 5 ml), then dried in vacuo to afford the product as a yellow solid (218 mg, 77%). 1 H NMR (500 MHz, DMSO-cfe) delta 12.05 (s, 1 H), 8.89 – 8.82 (m, 1 H), 8.03 – 7.99 (m, 1 H), 7.86 (s, 1 H), 7.58 (s, 2H), 7.13 – 7.09 (m, 1 H). LC/MS (System A): m/z (ESI+) = 307 [M(79Br)H+], 309 [M(81 Br)H+], Rt = 0.81 min, ELS purity = 100%.

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

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; MCCARTHY, Clive; HARGRAVE, Jonathan, David; HAY, Duncan, Alexander; SCHOFIELD, Thomas, Beauregard; WENT, Naomi; (261 pag.)WO2018/96325; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 51605-32-4, The chemical industry reduces the impact on the environment during synthesis 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, I believe this compound will play a more active role in future production and life.

Step a. 4-Ethoxycarbonyl-5-methyl-1-(2-nitro-4-trifluoromethylphenyl)-1H-imidazole A mixture of 4-fluoro-3-nitrobenzotrifluoride (20.5 ml, 146.5 mmol), ethyl 4-methyl-5-imidazolecarboxylate (23 g, 149.0 mmol), potassium carbonate (20.5 g, 148.5 mmol) and acetonitrile (200 ml) was stirred at 70¡ãC for 16 h. The solvent was removed under reduced pressure, and the residue submitted to flash chromatography on silica gel 60 eluding with toluene graduated to toluene/ethyl acetate (1:19) to give 42 g (84percent) of 4-ethoxycarbonyl-5-methyl-1-(2-nitro-5-trifluoromethylphenyl)-1H-imidazole. M.p. 139.5-140.5¡ãC.1H NMR (CDCl3): delta 1.45 (t, 3H), 2.35 (s, 3H), 4.40 (q, 2H), 7.50 (s, 1H), 7.65 (d, 1H), 8.10 (dd, 1H), 8.45 (d, 1H).

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

Reference:
Patent; NOVO NORDISK A/S; EP743945; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem