Category: 1151665-15-4

Electric Literature of 1151665-15-4, 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. 1151665-15-4, name is tert-Butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Ethyl 3-(2-chloro-7, 8-dihydro- 1, 6-naphthyridin- 6(5H)-yl)-2-methylpropanoate was prepared starting from tert-butyl 2-chloro- 7,8- dihydro- 1,6- naphthyridine- 6(5H) – carboxylate in accordance with scheme 6. Tert-butyl 2-chloro-7,8-dihydro-1,6- naphthyridine-6(5H)-carboxylate (3.22 g; 12 mmol; 1 eq) was dissolved in DCM (100 mL). TFA (13.7 g; 120 mmol; 10 eq) was added under stirring at RT. Themixture was stirred for 20h at RT. 50 mL of a saturated NaHCO3 solution was added followed by the addition of solid NaHCO3 while stirring until the pH of the aqueous phase was 7. After phase separation, the organic phase was dried with MgSO4 and evaporated. The aqueous phase was saturated with NaC1 under stirring foliowed by addition of 200 mL DCM and stirring for 30 mm. After phaseseparation, the organic phase was dried with MgSO4 and evaporated. The yield of the combined product 2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine was 2.01 g (11.92 mmol; 99%).

The synthetic route of tert-Butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; ABBVIE DEUTSCHLAND GMBH & CO. KG; LANGE, Udo; OCHSE, Michael; VAN DER KAM, Elizabeth; VAN BERGEIJK, Jeroen; TURNER, Sean; OELLIEN, Frank; WALLESER, Patrick; AMBERG, Wilhelm; HORNBERGER, Wilfried; GENESTE, Herve; MEZLER, Mario; HUTCHINS, Charles; (301 pag.)WO2017/36978; (2017); A1;,
Amide – Wikipedia,
Amide – 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. 1151665-15-4, name is tert-Butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: tert-Butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

To a solution of 9-cyclopentyl-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-amine (prepared as described in WO 2009/085185) (152 mg, 0.6 mmol) in dioxane (6 mL) were added tert-butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate (177 mg, 0.66 mmol), tris(dibenzylideneacetone)dipalladium (0) (28 mg, 0.030 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (52 mg, 0.090 mmol), and sodium t-butoxide (86 mg, 0.9 mmol). The reaction mixture thus obtained was heated at 150 C. under microwave irradiation for 1 hour. The reaction mixture was diluted with DCM, washed with brine, and then dried. The solvent was evaporated and the residue was purified by flash chromatography on silica gel eluting with 10% to 50% solvent A (DCM/MeOH/NH4OH, 100:10:1) in DCM to give the title compound as a light yellow solid (211 mg, 72% yield). 1H NMR (500 MHz, CDCl3) delta 1.52 (9H, s), 1.88-1.90 (2H, m), 2.14-2.21 (4H, m), 2.45-2.47 (2H, m), 2.92-2.94 (2H, m), 3.76-3.79 (2H, m), 4.59 (2H, m), 5.37 (1H, m), 7.49 (1H, d, J=10.0 Hz), 7.85 (1H, d, J=5.0 Hz), 8.14 (1H, br. s), 8.37 (1H, d, J=10.0 Hz), 8.52 (1H, d, J=5.0 Hz), 8.92 (1H, s), 9.11 (1H, s) ppm; LCMS m/z: 486 (M+1).

According to the analysis of related databases, 1151665-15-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Amgen Inc.; US2012/244110; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 1151665-15-4, 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. 1151665-15-4, name is tert-Butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Ethyl 3-(2-chloro-7, 8-dihydro- 1, 6-naphthyridin- 6(5H)-yl)-2-methylpropanoate was prepared starting from tert-butyl 2-chloro- 7,8- dihydro- 1,6- naphthyridine- 6(5H) – carboxylate in accordance with scheme 6. Tert-butyl 2-chloro-7,8-dihydro-1,6- naphthyridine-6(5H)-carboxylate (3.22 g; 12 mmol; 1 eq) was dissolved in DCM (100 mL). TFA (13.7 g; 120 mmol; 10 eq) was added under stirring at RT. Themixture was stirred for 20h at RT. 50 mL of a saturated NaHCO3 solution was added followed by the addition of solid NaHCO3 while stirring until the pH of the aqueous phase was 7. After phase separation, the organic phase was dried with MgSO4 and evaporated. The aqueous phase was saturated with NaC1 under stirring foliowed by addition of 200 mL DCM and stirring for 30 mm. After phaseseparation, the organic phase was dried with MgSO4 and evaporated. The yield of the combined product 2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine was 2.01 g (11.92 mmol; 99%).

The synthetic route of tert-Butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; ABBVIE DEUTSCHLAND GMBH & CO. KG; LANGE, Udo; OCHSE, Michael; VAN DER KAM, Elizabeth; VAN BERGEIJK, Jeroen; TURNER, Sean; OELLIEN, Frank; WALLESER, Patrick; AMBERG, Wilhelm; HORNBERGER, Wilfried; GENESTE, Herve; MEZLER, Mario; HUTCHINS, Charles; (301 pag.)WO2017/36978; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 1151665-15-4, 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 1151665-15-4 as follows.

To a solution of tert-butyl 2-chloro-7 ,8-dihydro-5H- 1 ,6-naphthyridine-6-carboxylate (1.0 g,3.7 mmol) in toluene (10 mL) was added KOH (0.6 g, 11.1 mmol) at 0 C and the mixture was stirred for 0.5 hr. To the resulting mixture was added a solution of BnOH (0.34 g, 5.6 mmol) in toluene (10 mL) followed by 18-crown-6 (100 mg) at 0C. The resulting mixture was heated with stirring at 130 C for 2 hrs and then filtered. The filtrate was concentrated in vacuo. Theresidue was purified by flash column to give tert-butyl 2-benzyloxy-7,8-dihydro-5H-1,6- naphthyridine-6-carboxylate (1 g).

According to the analysis of related databases, 1151665-15-4, 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, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics