Category: 917364-11-5

Application of 917364-11-5 , The common heterocyclic compound, 917364-11-5, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid, molecular formula is C8H10N2O2, 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 (c) N-((l s,4s)-4-(5-fluor o-2-(3-iodophenoxy)nicotinamido)cyclohexyl)-5,6,7,8- tetrahydroimidazo [ 1 ,2-a] pyridine-2-carboxamideTo a solution of 5,6,7, 8-tetrahydroimidazo[l,2-a]pyridine-2-carboxylic acid (0.183 g, 1.10 mmol) in dry DMF (10 niL) was added DIPEA (0.575 mL, 3.29 mmol) followed by HATU (0.418 g, 1.10 mmol). The mixture was allowed to stir for 10 min at RT. To this mixture was added the N-((ls,4s)-4-aminocyclohexyl)-5-fluoro-2-(3-iodophenoxy Nicotinamide (0.5 g, 1.10 mmol) and the mixture stirred overnight, poured onto water and the crude product collected by filtration, dried in vacuo to give the sub-title compound. Yield: 0.354 g 1H NMR (300 MHz, CDCl3) delta 8.36 (dd, J= 8.0, 3.0 Hz, IH), 8.06 (d, J= 3.1 Hz, IH), 7.86 (d, J= 7.3 Hz, IH), 7.64 (dt, J= 7.2, 1.3 Hz, IH), 7.55 (t, J= 1.8 Hz, IH), 7.40 (s, IH), 7.23 – 7.12 (m, 2H), 6.94 (d, J= 7.3 Hz, IH), 4.20 (s, IH), 4.08 (d, J= 3.5 Hz, IH), 3.98 (t, J= 8.6 Hz, 3H), 2.85 (q, J= 6.2 Hz, 2H), 2.05 – 1.73 (m, HH). [M+H]+ =604 (MultiMode+)

The synthetic route of 917364-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 917364-11-5 , The common heterocyclic compound, 917364-11-5, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid, molecular formula is C8H10N2O2, 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 (c) N-((l s,4s)-4-(5-fluor o-2-(3-iodophenoxy)nicotinamido)cyclohexyl)-5,6,7,8- tetrahydroimidazo [ 1 ,2-a] pyridine-2-carboxamideTo a solution of 5,6,7, 8-tetrahydroimidazo[l,2-a]pyridine-2-carboxylic acid (0.183 g, 1.10 mmol) in dry DMF (10 niL) was added DIPEA (0.575 mL, 3.29 mmol) followed by HATU (0.418 g, 1.10 mmol). The mixture was allowed to stir for 10 min at RT. To this mixture was added the N-((ls,4s)-4-aminocyclohexyl)-5-fluoro-2-(3-iodophenoxy Nicotinamide (0.5 g, 1.10 mmol) and the mixture stirred overnight, poured onto water and the crude product collected by filtration, dried in vacuo to give the sub-title compound. Yield: 0.354 g 1H NMR (300 MHz, CDCl3) delta 8.36 (dd, J= 8.0, 3.0 Hz, IH), 8.06 (d, J= 3.1 Hz, IH), 7.86 (d, J= 7.3 Hz, IH), 7.64 (dt, J= 7.2, 1.3 Hz, IH), 7.55 (t, J= 1.8 Hz, IH), 7.40 (s, IH), 7.23 – 7.12 (m, 2H), 6.94 (d, J= 7.3 Hz, IH), 4.20 (s, IH), 4.08 (d, J= 3.5 Hz, IH), 3.98 (t, J= 8.6 Hz, 3H), 2.85 (q, J= 6.2 Hz, 2H), 2.05 – 1.73 (m, HH). [M+H]+ =604 (MultiMode+)

The synthetic route of 917364-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 917364-11-5, 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid, 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, Application In Synthesis of 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid, blongs to pyridine-derivatives compound. Application In Synthesis of 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid

Example 137N-((ls,4s)-4-(5-fluoro-2-(4′-(3-(piperazin-l-yl)propyl)biphenyl-3- yloxyJnicotinamidoJcyclohexylJ-S^^^-tetrahydroimidazo [ 1 ,2-a] pyridine-2- carboxamide To a solution of tert-butyl 4-(3-(3′-(3-((ls,4s)-4-aminocyclohexylcarbamoyl)-5-fluoropyridin- 2-yloxy)biphenyl-4-yl)propyl)piperazine-l-carboxylate (150 mg, 0.24 mmol) in acetonitrile (2 mL) was added 5,6,7,8-tetrahydroimidazo[l,2-a]pyridine-2-carboxylic acid (39.5 mg, 0.24 mmol) and triethylamine (0.331 mL, 2.37 mmol). 1-Propanephosphonic acid cyclic anhydride, 1.57M solution in THF (0.159 mL, 0.25 mmol) was then added and the mixture stirred at RT for 1 h. The mixture was poured into sat NaHCO3 (aq) and the organics extracted into EtOAc (x2). The extractions were combined, dried (MgSO4) and evaporated to give a residue. This was dissolved in DCM (2 mL) to which TFA (2 mL) was added and the mixture stirred at RT for 20 min. The solvents were removed in vacuo and the residue dissolved in methanol and purified using reverse phase preparative chromatography using eluent = TFA(aq)/MeOH. The appropriate fractions were combined and evaporated to give a residue which on trituration with ether gave a solid. The solid was dried overnight under vacuum at 400C to give the title compound. Yield: 42 mg1H NMR (400 MHz, CD3OD) d 8.42 (d, J= 6.9 Hz, IH), 8.10 – 8.06 (m, 2H), 7.74 (s, IH), 7.53 (d, J= 8.2 Hz, 2H), 7.50 – 7.46 (m, 2H), 7.41 – 7.39 (m, IH), 7.28 (d, J= 8.2 Hz, 2H), 7.16 – 7.12 (m, IH), 4.15 – 4.08 (m, 3H), 3.98 – 3.91 (m, IH), 3.40 (t, J= 5.4 Hz, 4H), 3.21 – 3.16 (m, 4H), 2.97 – 2.89 (m, 4H), 2.72 (t, J= 7.4 Hz, 2H), 2.07 – 1.96 (m, 6H), 1.92 – 1.80 (m, 6H), 1.75 – 1.66 (m, 2H). MS: [M+H]+=680 (calc=680) (MultiMode+)

The synthetic route of 917364-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 917364-11-5, 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid, 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, Application In Synthesis of 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid, blongs to pyridine-derivatives compound. Application In Synthesis of 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid

Example 137N-((ls,4s)-4-(5-fluoro-2-(4′-(3-(piperazin-l-yl)propyl)biphenyl-3- yloxyJnicotinamidoJcyclohexylJ-S^^^-tetrahydroimidazo [ 1 ,2-a] pyridine-2- carboxamide To a solution of tert-butyl 4-(3-(3′-(3-((ls,4s)-4-aminocyclohexylcarbamoyl)-5-fluoropyridin- 2-yloxy)biphenyl-4-yl)propyl)piperazine-l-carboxylate (150 mg, 0.24 mmol) in acetonitrile (2 mL) was added 5,6,7,8-tetrahydroimidazo[l,2-a]pyridine-2-carboxylic acid (39.5 mg, 0.24 mmol) and triethylamine (0.331 mL, 2.37 mmol). 1-Propanephosphonic acid cyclic anhydride, 1.57M solution in THF (0.159 mL, 0.25 mmol) was then added and the mixture stirred at RT for 1 h. The mixture was poured into sat NaHCO3 (aq) and the organics extracted into EtOAc (x2). The extractions were combined, dried (MgSO4) and evaporated to give a residue. This was dissolved in DCM (2 mL) to which TFA (2 mL) was added and the mixture stirred at RT for 20 min. The solvents were removed in vacuo and the residue dissolved in methanol and purified using reverse phase preparative chromatography using eluent = TFA(aq)/MeOH. The appropriate fractions were combined and evaporated to give a residue which on trituration with ether gave a solid. The solid was dried overnight under vacuum at 400C to give the title compound. Yield: 42 mg1H NMR (400 MHz, CD3OD) d 8.42 (d, J= 6.9 Hz, IH), 8.10 – 8.06 (m, 2H), 7.74 (s, IH), 7.53 (d, J= 8.2 Hz, 2H), 7.50 – 7.46 (m, 2H), 7.41 – 7.39 (m, IH), 7.28 (d, J= 8.2 Hz, 2H), 7.16 – 7.12 (m, IH), 4.15 – 4.08 (m, 3H), 3.98 – 3.91 (m, IH), 3.40 (t, J= 5.4 Hz, 4H), 3.21 – 3.16 (m, 4H), 2.97 – 2.89 (m, 4H), 2.72 (t, J= 7.4 Hz, 2H), 2.07 – 1.96 (m, 6H), 1.92 – 1.80 (m, 6H), 1.75 – 1.66 (m, 2H). MS: [M+H]+=680 (calc=680) (MultiMode+)

The synthetic route of 917364-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 917364-11-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.917364-11-5, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid, molecular formula is C8H10N2O2, molecular weight is 166.18, as common compound, the synthetic route is as follows.

Example 12 (S)-N-(1-(3-(3-Chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxamide The title compound was prepared using the procedure described in Example 3(h) starting from 5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid (2.58 mmol, 428 mg) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluoro-benzonitrile (1.717 mmol, 479 mg). DMF (10 ml) was used as the solvent. The reaction mixture was diluted with water and extracted three times with DCM. The combined organics were washed twice with water. The organic phase was evaporated. The crude product was purified by flash chromatography. 515 mg of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): delta 1.07 (d, 3H), 1.78-1.94 (m, 4H), 2.76 (t, 2H), 3.95 (t, 2H), 4.24-4.31 (m, 1H), 4.33-4.46 (m, 2H), 7.01 (d, 1H), 7.43 (s, 1H), 7.84 (d, 1H), 7.90-7.95 (m, 1H), 8.00 (s, 1H), 8.08 (d, 1H).

The chemical industry reduces the impact on the environment during synthesis 917364-11-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ORION CORPORATION; Toermakaengas, Olli; Wohlfahrt, Gerd; Salo, Harri; Ramasurbamanian, Rathna Durga; Patra, Pranab Kumar; Martin, Arputharaj Ebenezer; Heikkinen, Terhi; Vesalainen, Anniina; Moilanen, Anu; Karjalainen, Arja; US2014/94474; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 917364-11-5, Adding some certain compound to certain chemical reactions, such as: 917364-11-5, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid,molecular formula is C8H10N2O2, 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 917364-11-5.

Example 91N-((ls,4s)-4-(2-(3′-(((3S,5R)-3,5-dimethylpiperazin-l-yl)methyl)-4′-hydroxybiphenyl-3- yloxy)-5-fluoronicotinamido)cyclohexyl)-5,6,7,8-tetr ahydroimidazo [ 1 ,2-a] pyridine-2- carboxamide To a solution of 5,6,7, 8-tetrahydroimidazo[l,2-a]pyridine-2-carboxylic acid (28.4 mg, 0.17 mmol) in acetonitrile (5 niL) was added DIPEA (0.057 niL, 0.34 mmol) and HATU (65.1 mg, 0.17 mmol). The mixture was allowed to stir at RT for 10 min before a solution of N-((ls,4s)- 4-aminocyclohexyl)-2-(3′-(((3S,5R)-3,5-dimethylpiperazin-l-yl)methyl)-4′-hydroxybiphenyl- 3-yloxy)-5-fluoronicotinamide (100 mg, 0.17 mmol) in acetonitrile (5 mL) with DIPEA (0.057 mL, 0.34 mmol) was added and the mixture stirred at RT for 30 mins. The reaction mixture was diluted in EtOAc (10 mL), washed with water, brine, dried (MgSO4) and evaporated to give a foam. This was purified by preparative HPLC to afford the title compound as a white solid. Yield: 31 mg1H NMR (400 MHz, CD3OD) delta 8.42 (d, J= 6.9 Hz, IH), 8.11 – 8.06 (m, 2H), 7.75 (s, IH), 7.57 – 7.42 (m, 4H), 7.38 (s, IH), 7.15 – 7.08 (m, IH), 6.92 (d, J= 8.5 Hz, IH), 4.16 – 4.07 (m, 5H), 3.98 – 3.89 (m, IH), 3.62 – 3.52 (m, 2H), 3.44 (d, J= 12.8 Hz, 2H), 2.95 (t, J= 6.2 Hz, 2H), 2.67 (t, J= 12.6 Hz, 2H), 2.10 – 1.64 (m, 12H), 1.32 (d, J= 6.7 Hz, 6H). MS: [M+H]+=696.4 (calc=696.3673) (MultiMode+)

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. 917364-11-5, 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 917364-11-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.917364-11-5, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid, molecular formula is C8H10N2O2, molecular weight is 166.18, as common compound, the synthetic route is as follows.

Step (a) 5,6,7,8-Tetrahydroimidazo[l,2-alpha]pyridin-2-ylmethanol5,6,7,8-Tetrahydroimidazo[l,2-«]pyridine-2-carboxylic acid (230 mg, 1.38 mniol) was suspended in THF (2.287 mL) and borane-tetrahydrofyuran complex (6.92 mL, 6.92 mmol) was added. The mixture was heated at reflux for 3 h then cooled to room temperature over a period of two days, then heated to reflux for a further 16 h. Methanol (10 mL) was then added dropwise and the reaction stirred for one hour then concentrated in vacuo. The crude product was dissolved in methanol (5 mL) and passed through an SCX column washing with methanol (100 mL) and eluting with 3.5N ammoniacal methanol (75 mL). The basic organic layer was concentrated to give the sub-title compound as a yellow oil (134 mg). 1H NMR (400 MHz, CDCl3) delta 6.72 (s, IH), 4.55 (s, 2H), 3.91 (t, J = 5.9 Hz, 2H), 2.85 (t, J = 6.3 Hz, 2H), 2.01 – 1.87 (m, 4H).

Statistics shows that 917364-11-5 is playing an increasingly important role. we look forward to future research findings about 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/84223; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem