Category: 89088-69-7

Reference of 89088-69-7,Some common heterocyclic compound, 89088-69-7, name is 1-Methyl-1H-imidazol-4-amine hydrochloride, molecular formula is C4H8ClN3, 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 2,4-dichlorofuro[3,2-d]pyrimidine (la) (0.71 g, 3.74 mmol; CAS 956034- 07-4) in 2-Propanol (20 mL) was added DIPEA (1.63 mL, 9.36 mmol), 1-methyl-1H-imidazol-4-amine hydrochloride (0.5 g, 3.74 mmol) and heated at reflux for 24 h. The reaction mixture was concentrated in vacuum to dryness and the residue obtained was triturated with water. The solid obtained was collected by filtration and dried in vacuum to afford 2-chloro-N-(l-methyl-lH-imidazol-4-yl)furo[3,2-d]pyrimidin-4-amine (lb) (550 mg,59 % yield) as brown solid; NMR (300 MHz, DMSO-^) delta 10.89 (s, 1H, D20exchangeable), 8.35 (d, J = 2.1 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.39 (d, J = 1.3 Hz, 1H), 7.03 (d, J = 2.1 Hz, 1H), 3.71 (s, 3H); MS (ES+): 250.3 (M+l), 272.3, 274.3 (M+Na), (ES-): 248.2 (M-l).

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-4-amine hydrochloride, its application will become more common.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 89088-69-7, These common heterocyclic compound, 89088-69-7, name is 1-Methyl-1H-imidazol-4-amine 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.

To a solution of 2,4-dichlorofuro[3,2-d]pyrimidine (la) (0.71 g, 3.74 mmol; CAS 956034- 07-4) in 2-Propanol (20 mL) was added DIPEA (1.63 mL, 9.36 mmol), 1-methyl-1H-imidazol-4-amine hydrochloride (0.5 g, 3.74 mmol) and heated at reflux for 24 h. The reaction mixture was concentrated in vacuum to dryness and the residue obtained was triturated with water. The solid obtained was collected by filtration and dried in vacuum to afford 2-chloro-N-(l-methyl-lH-imidazol-4-yl)furo[3,2-d]pyrimidin-4-amine (lb) (550 mg,59 % yield) as brown solid; NMR (300 MHz, DMSO-^) delta 10.89 (s, 1H, D20exchangeable), 8.35 (d, J = 2.1 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.39 (d, J = 1.3 Hz, 1H), 7.03 (d, J = 2.1 Hz, 1H), 3.71 (s, 3H); MS (ES+): 250.3 (M+l), 272.3, 274.3 (M+Na), (ES-): 248.2 (M-l).

Statistics shows that 1-Methyl-1H-imidazol-4-amine hydrochloride is playing an increasingly important role. we look forward to future research findings about 89088-69-7.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 89088-69-7, name is 1-Methyl-1H-imidazol-4-amine 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 89088-69-7, category: imidazoles-derivatives

A mixture of 4-benzenesulfonyl-2,6-dichloro-pyridine (0.40 g, 1.39 mmol), 1-methyl- lH-imidazole-4-amine hydrochloride (0.22 g, 1.67 mmol) and DIPEA (0.7 mL, 4.16 mmol) in anhydrous DMSO (4.6 mL) was flushed with nitrogen and heated at 120 C in a sealed microwave vial (plastic lid) for 2 h. The mixture was then partitioned between EtOAc (20 mL) and saturated aqueous ammonium chloride solution (10 mL) and the phases separated. The aqueous phase was extracted with EtOAc (2 x 10 mL) and the combined organic extracts were washed with water (10 mL) and brine (10 mL), dried over MgS04, filtered and concentrated in vacuo. The crude material was purified by flash silica chromatography (eluting with 1-8% MeOH in DCM) to give the title compound as a yellow solid (0.14g, 82% purity, 24% yield). MS: m/z = 349.0 (M+H)+.

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Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BROMIDGE, Steven; BURCH, Jason; HEIFETZ, Alexander; KRULLE, Thomas; MONTALBETTI, Christian A.G.N.; PEI, Zhonghua; PEREZ-FUERTES, Yolanda; TRANI, Giancarlo; (223 pag.)WO2016/1341; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 89088-69-7, name is 1-Methyl-1H-imidazol-4-amine 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. COA of Formula: C4H8ClN3

Intermediate 69; 6-Chloro-iV-( 1 -methyl- lH-imidazol-4-vO- 1 -(tetrahvdro-2H-pyran-2-vO- 1 H-pyrazolo [3 A- dlpyrimidin-4-amineTo a solution of 4,6-dichloro-l-(tetrahydro-2H-pyran-2-yl)-lH-pyrazolo[3,4-d]pyrimidine(Intermediate 70, 3.168 g, 11.60 mmol) in ethanol (60 mL), was added TEA (4.04 mL, 29.00 mmol) followed by 1 -methyl- lH-imidazol-4-amine hydrochloride (Intermediate 36, 1.549 g,11.60 mmol). The resulting mixture was heated at 600C for 2 hours. Evaporation of the volatiles under reduced pressure gave a residue, which was purified utilizing ISCO (EtOAc/hexanes0->80%) to give the title product (1.56g).LCMS: 334 [M+Eta]+.

The synthetic route of 1-Methyl-1H-imidazol-4-amine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
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

Electric Literature of 89088-69-7, A common heterocyclic compound, 89088-69-7, name is 1-Methyl-1H-imidazol-4-amine hydrochloride, molecular formula is C4H8ClN3, 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 1 -methyl- lH-imidazol-4-amine hydrochloride (Intermediate 36 , 16.39 g, 122.74 mmol) and 2,4-dichloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-J]pyrimidine (Intermediate 9, 21 g, 61.37 mmol) and DIPEA (42.9 ml, 245.47 mmol) in ethanol (264 ml) were heated at 88 0C overnight. The reaction mixture was cooled to 0 0C and filtered to provide 2-chloro-N-(l -methyl- lEta-imidazol-4-yl)-7-tosyl-7Eta-pyrrolo[2,3-d]pyrimidin-4-amine contaminated with DIPEA. The solid was dissolved in EtOAc (400 ml) and the solution was washed with water (3×100 ml). During the process, the title product crashed out of solution and collected through filtration. Concentration of the mother liquor provided additional title product (total=18.8 g, 76%). LCMS: 403 [M+H]+.1H NMR (300 MHz, DMSO-J6) deltappm 10.75 (br. s., 1 H), 7.96 (d, 2 H), 7.63 (d, 1 H),7.40 – 7.55 (m, 3 H), 7.35 (s, 1 H), 7.23 (br. s., 1 H), 3.68 (s, 3 H), 2.37 (s, 3 H)

The synthetic route of 89088-69-7 has been constantly updated, and we look forward to future research findings.

Reference:
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

Application of 89088-69-7,Some common heterocyclic compound, 89088-69-7, name is 1-Methyl-1H-imidazol-4-amine hydrochloride, molecular formula is C4H8ClN3, 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 2,4-dichlorofuro[3,2-d]pyrimidine (la) (0.71 g, 3.74 mmol; CAS 956034- 07-4) in 2-Propanol (20 mL) was added DIPEA (1.63 mL, 9.36 mmol), 1-methyl-1H-imidazol-4-amine hydrochloride (0.5 g, 3.74 mmol) and heated at reflux for 24 h. The reaction mixture was concentrated in vacuum to dryness and the residue obtained was triturated with water. The solid obtained was collected by filtration and dried in vacuum to afford 2-chloro-N-(l-methyl-lH-imidazol-4-yl)furo[3,2-d]pyrimidin-4-amine (lb) (550 mg,59 % yield) as brown solid; NMR (300 MHz, DMSO-^) delta 10.89 (s, 1H, D20exchangeable), 8.35 (d, J = 2.1 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.39 (d, J = 1.3 Hz, 1H), 7.03 (d, J = 2.1 Hz, 1H), 3.71 (s, 3H); MS (ES+): 250.3 (M+l), 272.3, 274.3 (M+Na), (ES-): 248.2 (M-l).

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-4-amine hydrochloride, its application will become more common.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 89088-69-7,Some common heterocyclic compound, 89088-69-7, name is 1-Methyl-1H-imidazol-4-amine hydrochloride, molecular formula is C4H8ClN3, 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.

Intermediate 23; 2-Chloro-Lambda/-(l-methyl-lH-imidazol-4-yl)pyridor2,3-dlpyrimidin-4-amine1 -Methyl- lH-imidazol-4-amine hydrochloride (Intermediate 36, 167 mg, 1.72 mmol), 2,4- dichloropyrido[2,3-d]pyrimidine (500 mg, 2.50 mmol) were suspended in ethanol (10 mL) and TEA (0.24mL, 1.72 mmol) was added. The reaction mixture was heated at 700C overnight and the title product was obtained after filtration (421mg).1H NMR (300 MHz, DMSO-d6) delta ppm 11.33 (s, 1 H) 9.16 (d, 1 H) 9.01 (s, 1 H) 7.54-7.72(m, 3H) 3.75 (s, 3 H). 103496-1PLCMS: 261 [M+H]4

The synthetic route of 89088-69-7 has been constantly updated, and we look forward to future research findings.

Reference:
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

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. Quality Control of 1-Methyl-1H-imidazol-4-amine hydrochloride

Intermediate 432-Chloro-7-(2-fluoroethyl)-Lambda/-(l -methyl- lH-imidazol-4-yl)-7H-pyrrolo[2,3-dlpyrimidin-4-amineThe solution of 2,4-dichloro-7-(2-fluoroethyl)-7H-pyrrolo[2,3-d]pyrimidine (Intermediate 44, 600 mg, 2.56 mmol) and 1 -methyl- lH-imidazol-4-amine hydrochloride (Intermediate 36, 523 mg, 3.08 mmol) was added to DIPEA (2686 mul, 15.38 mmol) in ethanol (5859 mul) and the reaction mixture was heated at 90 0C for 24 hours. Additional 1 -methyl- lH-imidazol-4-amine hydrochloride (Intermediate 36, 523 mg, 3.08 mmol) and DIPEA (2686 mul, 15.38 mmol) added to the reaction mixture and the mixture was heated at 90 0C for another 24 hours. The volatiles were removed under reduced pressure to afford a residue, which was dissolved in DCM/MeOH (10%) and washed with water. The organic layer was concentrated in vacuum, followed by purification by reversed phase HPLC (Gilson chromatography, 0%->50% MeCN/0.1% TFA H2O) to yield the title product (454 mg). LCMS: 297 [M+H]+.

According to the analysis of related databases, 89088-69-7, the application of this compound in the production field has become more and more popular.

Reference:
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

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

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. 89088-69-7, name is 1-Methyl-1H-imidazol-4-amine hydrochloride, A new synthetic method of this compound is introduced below., SDS of cas: 89088-69-7

Intermediate 19; 1 -Ethyl-iV-d -methyl- lH-imidazol-4-yl)-6-(methylsulfonyl)- lH-pyrazolo[3 ,4-