Category: 16042-25-4

Some common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, molecular formula is C4H4N2O2, 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. Safety of 2-Imidazolecarboxylic acid

Example 45 lambda/-[6-(1H-lndol-4-yl)-1H-indazol-4-yl]-1H-imidazole-2-carboxamide 1H-lmidazole-2-carboxylic acid (17mg) (available from Maybridge), HATU (63mg) and 6- (1 H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2/-/-indazol-4-amine (50mg) were dissolved in anhydrous DMF (3ml) and then treated with DIPEA (0.052ml) and stirred at RT for 15h. The mixture was treated with methanol (3ml) and then macroporous-tosic acid resin (170mg; 4.4mmol/g) then stirred for 15h. The mixture was then treated with 0.88 ammonia solution (0.600ml), stirred for 10min, then filtered and solvent blown off under a stream of nitrogen. The crude residue was purified by mass directed preparative HPLC (Method A) to give the title compound. LC/MS R1 0.87min m/z 343 [MH+]. Method B

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16042-25-4, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/147188; (2009); 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

16042-25-4, name is 2-Imidazolecarboxylic acid, 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. Application In Synthesis of 2-Imidazolecarboxylic acid

) A/-(3,5-Difluorophenyl)-1 H-imidazole-2-carboxamideTo a solution of 1 /-/-imidazole-2-carboxylic acid (2.50 g, 22.3 mmol) in DMF (30 mL) were added 3,5-difluoroaniline (2.23 mL, 22.3 mmol), EDC-HCI (6.41 g, 33.46 mmol) and HOBt (4.52 g, 33.46 mmol). The reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuum and the crude was dissolved in dichloromethane. The solution was washed with a diluted aqueous solution of potassium carbonate, dried over sodium sulphate, filtered and concentrated. 2.75 g (55% yield) of the title compound were obtained as a solid.LRMS (m/z): 224 (M+1 )

The synthetic route of 16042-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; BERNAL ANCHUELA, Francisco Javier; CARRASCAL RIERA, Marta; CATURLA JAVALOYES, Juan Francisco; GRACIA FERRER, Jordi; MATASSA, Victor Giulio; TERRICABRAS BELART, Emma; TALTAVULL MOLL, Joan; ERRA SOLA, Montserrat; WO2012/146666; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 16042-25-4, name is 2-Imidazolecarboxylic acid, 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 16042-25-4, Computed Properties of C4H4N2O2

Step 1: To a solution of compound 1c (1 equivalent) in dichloromethane, compound 14a (1.5 eq.) was added sequentially.HOAT (1.5 eq.), HATU (2 eq.), DIPEA (6 eq.), stirred at room temperature for 12 hours.The solvent is then sparged off and directly isolated by column chromatography to afford intermediate 14b.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Imidazolecarboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Chinese Academy Of Sciences Shanghai Life Sciences Institute; Zhang Ao; Gao Daming; Ni Jiabin; Hu Hongli; Ding Chunyong; (55 pag.)CN107814792; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

16042-25-4, name is 2-Imidazolecarboxylic acid, 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. Application In Synthesis of 2-Imidazolecarboxylic acid

A mixture of 1 H-imidazole-2-carboxylic acid (15 mg, 0.13 mmol), aniline lnt-9a (54 mg, 0.13 mmol), diisopropylethyiamine (46 muIota_, 0.27 mmoi) and HATU (56 mg, 0.15 mmol) was stirred in N,N-dimethylformamide (3 mL) at r.t. overnight. Water and ethyl acetate were added, and the layers were separated. The separated organic layer was washed with water. The separated organic layer was dried (MgS04) and filtered. The solvents were removed in vacuo and chromatographic purification (ethyl acetate – hexane) of the residue gave amide lnt-9b (21 mg, 32%) as a white solid.

The synthetic route of 16042-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; TSUI, Hon-Chung; PALIWAL, Sunil; KIM, Hyunjin, M.; KEREKES, Angela, D.; CAPLEN, Mary Ann; ESPOSITE, Sara, J.; MCKITTRICK, Brian, A.; FISCHMANN, Thierry Olivier; DOLL, Ronald, J.; RAINKA, Matthew Paul; LI, Ang; WO2011/149874; (2011); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

16042-25-4, The chemical industry reduces the impact on the environment during synthesis 16042-25-4, name is 2-Imidazolecarboxylic acid, I believe this compound will play a more active role in future production and life.

To a solution of 1H-imidazole-2-carboxylic acid (0.179) in N,N-dimethylformamide (DMF) (3 mL) was added alanine tert-butyl ester hydrochloride (0.22 g), diisopropylethyl amine (0.27 mL) and HOBT (0.41 g) before cooling to 0 C. and the reaction mixture was then treated with EDC HCl (0.32 g). The cooling bath was removed and the reaction mixture was stirred at ambient temperature for 18 hrs before being diluted with ethyl acetate and washed with water and brine, dried (MgSO4) and concentrated at reduced pressure. The residue was purified by silica gel chromatography (30% ethyl acetate in hexanes) to afford the sub-title compound as a colourless oil (0.263 g, 73%): 1H NMR 400 MHz CDCl3 1.50 (9H, s), 1.51 (3H, d, J 7.2), 3.70 (1H, m), 7.28 (2H, s), 7.78 (1H, d, J 7.6), 11.49 (1H, br s).

The chemical industry reduces the impact on the environment during synthesis 2-Imidazolecarboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Randle, John C.R.; US2005/267101; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 16042-25-4, name is 2-Imidazolecarboxylic acid, 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 16042-25-4, 16042-25-4

PREPARATION 33 1-amino-N-phenyl-1H-imidazole-2-carboxamide a) N-phenyl-1H-imidazole-2-carboxamide To a solution of 1H-imidazole-2-carboxylic acid (0.975 g, 8.7 mmol) in DMF (30 mL) were added aniline (0.67 mL, 8.7 mmol), EDC¡¤HCl (2.54 g, 13.05 mmol) and HOBt (1.76 g, 13.05 mmol). The reaction mixture was stirred at room temperature for 21 hours. Then, it was poured into water and extracted with ethyl acetate. The combined organic layer was dried over sodium sulphate, filtered and concentrated. The crude residue was purified by flash chromatography (2% to 3% methanol in dichloromethane) to yield 1.55 g (96% yield) of the title compound. LRMS (m/z): 188 (M+1)+.

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-Imidazolecarboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Almirall, S.A.; EP2518070; (2012); 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 16042-25-4 as follows. 16042-25-4

A mixture of 5-methyl-2- (2-pyridyl)-5 ,6,7 ,8-tetrahydropyrido [4,3 d]pyrimidinetrifluoroacetic acid salt (100 mg, 442 imol, the product of step 2 in Example 34), 1H-imidazole-2-carboxylic acid (74.3 mg, 663 j.imol), HATU (336 mg, 884 imol) and DIPEA (171 mg, 1.33 mmol) in DMF (5 mL) was stirred at rt overnight. The resulting mixture was poured into water and extracted with DCM (30 ml) twice. The combined organic layer was dried over anhydrous Na2504 and concentrated in vacuo and the residue was purified by prep-HPLC to give 1H- imidazol-2-yl-[5-methyl-2-(2-pyridyl)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]methanone(76 mg) as off-white solid. ?H NMR (400 MHz, Methanol-d4) oe: 8.59-8.8 1 (m, 2H), 8.36-8.48(m, 1H), 7.84-7.97 (m, 1H), 7.36-7.49 (m, 1H), 6.99-7.28 (m, 2H), 6.78-6.94 (m, 0.3H), 5.50-5.88 (m, 1.2H), 4.80-5.01 (m, 0.5H), 3.23-3.69 (m, 1.5H), 3.03 (br d, 1.5H), 1.45-1.77 (m, 3H).MS obsd. (ESI)[(M+H)]: 321.

According to the analysis of related databases, 16042-25-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Jianhua; WANG, Min; YANG, Song; (84 pag.)WO2018/83106; (2018); 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 16042-25-4 as follows. 16042-25-4

A mixture of 5-methyl-2- (2-pyridyl)-5 ,6,7 ,8-tetrahydropyrido [4,3 d]pyrimidinetrifluoroacetic acid salt (100 mg, 442 imol, the product of step 2 in Example 34), 1H-imidazole-2-carboxylic acid (74.3 mg, 663 j.imol), HATU (336 mg, 884 imol) and DIPEA (171 mg, 1.33 mmol) in DMF (5 mL) was stirred at rt overnight. The resulting mixture was poured into water and extracted with DCM (30 ml) twice. The combined organic layer was dried over anhydrous Na2504 and concentrated in vacuo and the residue was purified by prep-HPLC to give 1H- imidazol-2-yl-[5-methyl-2-(2-pyridyl)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]methanone(76 mg) as off-white solid. ?H NMR (400 MHz, Methanol-d4) oe: 8.59-8.8 1 (m, 2H), 8.36-8.48(m, 1H), 7.84-7.97 (m, 1H), 7.36-7.49 (m, 1H), 6.99-7.28 (m, 2H), 6.78-6.94 (m, 0.3H), 5.50-5.88 (m, 1.2H), 4.80-5.01 (m, 0.5H), 3.23-3.69 (m, 1.5H), 3.03 (br d, 1.5H), 1.45-1.77 (m, 3H).MS obsd. (ESI)[(M+H)]: 321.

According to the analysis of related databases, 16042-25-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Jianhua; WANG, Min; YANG, Song; (84 pag.)WO2018/83106; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The chemical industry reduces the impact on the environment during synthesis 16042-25-4, name is 2-Imidazolecarboxylic acid, I believe this compound will play a more active role in future production and life. 16042-25-4

5 (1.00 g, 3.30 mmol) and 1H-imidazole-2-carboxylic acid(0.40 g, 3.60 mmol) were dissolved in 3 mL sulfolane, and 12 mLPOCl3 was added. The reaction mixturewas stirred at 85 C for 18 h,then cooled to room temperature, poured into 200 mL ice water.NaOH was added to adjust the PH to 7. The mixturewas filtered anddried in vacuo to give 92 mg of 11-3 as gray solid: 7% yield. 1H NMR(300 MHz, DMSO-d6) delta 13.83 (s, 1H), 8.77 (d, J = 5.4 Hz, 1H), 8.01 (d,J = 9.0 Hz, 1H), 7.52 (s, 1H), 7.36 (d, J = 2.5 Hz, 1H), 7.28 (d, J =5.2 Hz,2H), 7.18 (dd, J= 9.2, 2.6 Hz, 1H), 5.82 (s, 2H), 3.90 (s, 3H); m.p.:205-207 C; HRMS (ESI+) m/z 380.0914 (380.0924 calcd forC17H14N7O2S+, [M+H]+).

The chemical industry reduces the impact on the environment during synthesis 16042-25-4. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yuan, Haoliang; Liu, Qiufeng; Zhang, Li; Hu, Shihe; Chen, Tiantian; Li, Huifang; Chen, Yadong; Xu, Yechun; Lu, Tao; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 491 – 502;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem