Category: 2770-01-6

Electric Literature of 2770-01-6, A common heterocyclic compound, 2770-01-6, name is 4-Chloro-1H-imidazo[4,5-c]pyridine, molecular formula is C6H4ClN3, 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.

Step A Preparation of 3-[4-(1-carbomethoxy-1-(3,4-methylenedioxy-phenyl)methoxy)-3,5-dipropylphenylmethyl]-4-chloro-3H-imidazo[4,5-c]pyridine Cesium carbonate (117.3 mg, 0.36 mmol) was added to 4-chloroimidazo[4,5-c]pyridine (25 mg, 0.18 mmol) in DMF (2 mL) at room temperature under nitrogen. After stirring for 15 min, a solution of 4-(1-carbomethoxy- 1-(3,4-methylenedioxyphenyl)methoxy)-3,5-dipropylbenzyl bromide (106.5 mg, 0.23 mmol) in DMF (2 mL) was added and the mixture stirred at room temperature for 12 h. The mixture was poured onto ice/water and the crude product that precipitated was collected by filtration. The crude material was pre-adsorbed on silica gel and chromatographed (0 to 50% hexane/ethyl acetate) to afford the title compound (25 mg). 1 H-NMR (CDCl3): delta 8.24 (d, 1H), 8.00 (s, 1H), 7.68 (d, 1H), 7.04 (s, 1H), 6.88 (d, 1H), 6.82 (s, 2H), 6.75 (d, 1H), 5.96 (s, 2H), 5.60 (s,2H), 5.00 (s, 1H), 3.71 (s,3H), 2.35 (m, 4H), 1.40 (m, 4H), 0.78 (t, 6H).

The synthetic route of 2770-01-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5334598; (1994); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 2770-01-6, 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. 2770-01-6, name is 4-Chloro-1H-imidazo[4,5-c]pyridine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The chiral cyclopentenyl moiety 5 (below) was prepared from D-ribose in 8 steps following a previously reported synthetic method via a chiral induction, a regioselective protection of hydroxy group and ring-closing metathesis with 0.1 mole% of the 2nd generation Grubbs catalyst as key steps. 10; The other key intermediate 7 was synthesized according to the previously reported procedure11 from commercially available 4-amino-2-chloropyridine (6) in 4 steps (overall 54% yield) as shown in Scheme 1. Mitsunobu reaction of 7 with 5 provided a mixture of the N9- and N7-regioisomers (8:9 = 2:1) in 94% yield. The separation of the desired product (8) from the reaction mixture was difficult by silica gel column [isolated yields: 20% (8) and 20% (9), respectively]. The ratio of the two isomers was determined by 1H-NMR, and their configuration was identified by Nuclear Overhouser Effect (ID-NOE), which indicated the interaction between the C1 ‘-H and the aromatic C3-H of compound 8, whereas the same effect was not present in compound 9.

The synthetic route of 4-Chloro-1H-imidazo[4,5-c]pyridine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF GEORGIA RESEARCH FOUNDATION, INC.; WO2007/47793; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 2770-01-6, A common heterocyclic compound, 2770-01-6, name is 4-Chloro-1H-imidazo[4,5-c]pyridine, molecular formula is C6H4ClN3, 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.

Step A Preparation of 3-[4-(1-carbomethoxy-1-(3,4-methylenedioxy-phenyl)methoxy)-3,5-dipropylphenylmethyl]-4-chloro-3H-imidazo[4,5-c]pyridine Cesium carbonate (117.3 mg, 0.36 mmol) was added to 4-chloroimidazo[4,5-c]pyridine (25 mg, 0.18 mmol) in DMF (2 mL) at room temperature under nitrogen. After stirring for 15 min, a solution of 4-(1-carbomethoxy- 1-(3,4-methylenedioxyphenyl)methoxy)-3,5-dipropylbenzyl bromide (106.5 mg, 0.23 mmol) in DMF (2 mL) was added and the mixture stirred at room temperature for 12 h. The mixture was poured onto ice/water and the crude product that precipitated was collected by filtration. The crude material was pre-adsorbed on silica gel and chromatographed (0 to 50% hexane/ethyl acetate) to afford the title compound (25 mg). 1 H-NMR (CDCl3): delta 8.24 (d, 1H), 8.00 (s, 1H), 7.68 (d, 1H), 7.04 (s, 1H), 6.88 (d, 1H), 6.82 (s, 2H), 6.75 (d, 1H), 5.96 (s, 2H), 5.60 (s,2H), 5.00 (s, 1H), 3.71 (s,3H), 2.35 (m, 4H), 1.40 (m, 4H), 0.78 (t, 6H).

The synthetic route of 2770-01-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5334598; (1994); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 2770-01-6, These common heterocyclic compound, 2770-01-6, name is 4-Chloro-1H-imidazo[4,5-c]pyridine, 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 improve the selectivity for the ^-substitution by blocking the N7-position with sterically demanded groups, 6-chloro-3-deazapurine (7) was converted to N-protected 3- deazaadenine derivatives (21a-b) (Scheme 2). Our initial attempts to convert the 6-chloride to the N6-amino group by methanolic ammonia or hydrazine/Raney-nickel gave 3-deazaadenine (13) in poor yields. However, the reaction of 7 with NaN3 or LiN3 provided 3-deaza- tetrazolopurine (12)la in about 80% and 82% yields with about 20% of starting material (7), which could not be removed from 12 (Table 1), respectively. The same reaction for 3-deaza- tetrazolopurine (12) was investigated by addition of an ionic liquid (DMF- [emim]BF4).13 LiN3 (20% in water) and DMF-[emim]BF4 ionic liquid (10:1 v/v) at 80 0C for 6 h provided 3- deaza-tetrazolopurine (12) in quantitative yield without 7. The ionic liquid was readily recovered by simple filtration, and recycled.14

Statistics shows that 4-Chloro-1H-imidazo[4,5-c]pyridine is playing an increasingly important role. we look forward to future research findings about 2770-01-6.

Reference:
Patent; UNIVERSITY OF GEORGIA RESEARCH FOUNDATION, INC.; WO2007/47793; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 2770-01-6, 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. 2770-01-6, name is 4-Chloro-1H-imidazo[4,5-c]pyridine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The chiral cyclopentenyl moiety 5 (below) was prepared from D-ribose in 8 steps following a previously reported synthetic method via a chiral induction, a regioselective protection of hydroxy group and ring-closing metathesis with 0.1 mole% of the 2nd generation Grubbs catalyst as key steps. 10; The other key intermediate 7 was synthesized according to the previously reported procedure11 from commercially available 4-amino-2-chloropyridine (6) in 4 steps (overall 54% yield) as shown in Scheme 1. Mitsunobu reaction of 7 with 5 provided a mixture of the N9- and N7-regioisomers (8:9 = 2:1) in 94% yield. The separation of the desired product (8) from the reaction mixture was difficult by silica gel column [isolated yields: 20% (8) and 20% (9), respectively]. The ratio of the two isomers was determined by 1H-NMR, and their configuration was identified by Nuclear Overhouser Effect (ID-NOE), which indicated the interaction between the C1 ‘-H and the aromatic C3-H of compound 8, whereas the same effect was not present in compound 9.

The synthetic route of 4-Chloro-1H-imidazo[4,5-c]pyridine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF GEORGIA RESEARCH FOUNDATION, INC.; WO2007/47793; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2770-01-6, name is 4-Chloro-1H-imidazo[4,5-c]pyridine, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: chlorides-buliding-blocks

A mixture of 200 mg (1.3 mmol) of 4-chloro-lH-imidazo[4,5-c]pyridine [J. A.Montgomery and K. Hewson, J. Med. Chern., 8, 708 (1965)], 0.253 mL (261 mg, 5.2 mmol) of hydrazinehydrate, and 5 mL of ethanol was stirred at room temperature overnight. The precipitate was collectedon a filter, washed with a little ethanol, and dried to give the title compound as a solid. LC-MS 150(M+l).

The synthetic route of 2770-01-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2006/23750; (2006); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 2770-01-6, name is 4-Chloro-1H-imidazo[4,5-c]pyridine, A new synthetic method of this compound is introduced below., Quality Control of 4-Chloro-1H-imidazo[4,5-c]pyridine

To improve the selectivity for the ^-substitution by blocking the N7-position with sterically demanded groups, 6-chloro-3-deazapurine (7) was converted to N-protected 3- deazaadenine derivatives (21a-b) (Scheme 2). Our initial attempts to convert the 6-chloride to the N6-amino group by methanolic ammonia or hydrazine/Raney-nickel gave 3-deazaadenine (13) in poor yields. However, the reaction of 7 with NaN3 or LiN3 provided 3-deaza- tetrazolopurine (12)la in about 80% and 82% yields with about 20% of starting material (7), which could not be removed from 12 (Table 1), respectively. The same reaction for 3-deaza- tetrazolopurine (12) was investigated by addition of an ionic liquid (DMF- [emim]BF4).13 LiN3 (20% in water) and DMF-[emim]BF4 ionic liquid (10:1 v/v) at 80 0C for 6 h provided 3- deaza-tetrazolopurine (12) in quantitative yield without 7. The ionic liquid was readily recovered by simple filtration, and recycled.14

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; UNIVERSITY OF GEORGIA RESEARCH FOUNDATION, INC.; WO2007/47793; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 2770-01-6, name is 4-Chloro-1H-imidazo[4,5-c]pyridine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H4ClN3

Reference Example 11 3-{[2-(Trimethylsilyl)ethoxy]methyl}-3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one 1-{[2-(Trimethylsilyl)ethoxy]methyl}-1,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one [Show Image] Diethoxymethyl acetate (15 mL) was added to 2-chloropyridine-3,4-diamine (480 mg) and the resulting mixture was stirred at room temperature for 12 hours. To the mixture was added 1N hydrochloric acid and the precipitate formed was filtered, washed with diethyl ether and then dried to obtain a crude product (400 mg), 4-chloro-1H-imidazo[4,5-c]pyridine as a brown solid. The spectrum of this compound is as follows: 1H NMR (400 MHz, CD3OD) delta 9.45 (s, 1H), 8.51 (d, J = 5.9 Hz, 1H), 7.94 (d, J = 5.9 Hz, 1H). MS (ESI+) 154 (M+ +1, 100%). A hydrochloric acid/methanol solution (25 mL, methanol component 80-90%) was added to this solid (220 mg) and the resulting mixture was heated under reflux for 30 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure, and the resulting residue was washed with diethyl ether and dried to obtain a crude product (150 mg), 3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one as a brown solid. The spectrum of this compound is as follows: 1H NMR (400 MHz, CD3OD) delta 9.40 (s, 1H), 7.58 (d, J = 7.2 Hz, 1H), 6.87 (d, J = 7.2 Hz, 1H). MS (ESI+) 136 (M++1, 100%). Under a nitrogen atmosphere, sodium hydride (134 mg, a 60% oil dispersion) was added to N,N-dimethylformamide (15 mL) and the resulting suspension was cooled to -15C. To the suspension was added 3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one (360 mg) and the resulting mixture was stirred at room temperature for 30 minutes. Then, chloro-2-(trimethylsilyl)ethoxymethane (0.550 mL) was added dropwise thereto, followed by stirring at room temperature for 20 hours. Water was added to the reaction solution, followed by extraction with chloroform. The organic layer was washed with water and a saturated aqueous sodium chloride solution, dried over sodium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by a silica gel column chromatography (developing solvent: chloroform/methanol = 20/1 to 10/1) to obtain 3-{[2-(trimethylsilyl)ethoxy]methyl}-3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one (119 mg) and 1-{[2-(trimethyl-silyl)ethoxy]methyl}-1,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one (113 mg) each as a white solid. 3-{[2-(Trimethylsilyl)ethoxy]methyl}-3,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one 1H NMR (400 MHz, CDCl3) delta 11.49 (bs, 1H), 8.03 (s, 1H), 7.16 (m, 1H), 6.77 (d, J = 7.0 Hz, 1H), 5.91 (s, 2H), 3.66 (t, J = 8.2 Hz, 2H), 0.93 (t, J = 8.2 Hz, 2H), – 0.04 (s, 9H). MS (ESI+) 266 (M++1, 100%). 1-{[2-(Trimethylsilyl)ethoxy]methyl}-1,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one 1H NMR (400 MHz, CDCl3) delta 10.97 (bs, 1H), 7.84 (s, 1H), 7.21 (m, 1H), 6.56 (d, J = 7.1 Hz, 1H), 5.45 (s, 2H), 3.51 (t, J = 8.2Hz, 2H), 0.90 (t, J = 8.2 Hz, 2H), – 0.03 (s, 9H). MS (ESI+) 266 (M++1, 100%).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2770-01-6.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP1690863; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics