Category: 111042-89-8

Reference of 111042-89-8 ,Some common heterocyclic compound, 111042-89-8, molecular formula is C9H8N2O2S, 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.

3-[3-(3,4-Dihydroquinolin-1(2H)-ylsulfonyl)phenyl]pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidin-2,4(1H,3H)-dione [Show Image] To a 0.75N solution (1.16 ml) of methyl 3-aminothieno[2,3-b]pyridine-2-carboxylate in dichloromethane, a 2.25N solution (1.12 ml) of triethylamine in dichloromethane was added, and then a 0.25N solution (1.36 ml) of triphosgene in dichloromethane was added dropwise on stirring to the mixture under nitrogen atmosphere at -78C. The cold bath was removed, the mixture was stirred for additional 20 min, and the reaction mixture was concentrated under reduced pressure. The residue was diluted with THF (4.2 ml). A solution of 3-(3,4-dihydro-1(2H)-quinolinylsulfonyl)aniline (0.25N) and DMAP (0.375N) in THF (1.12 ml) was added dropwise, and the mixture was stirred at room temperature for 25 hr. Insoluble triethylamine hydrochloride was filtrated, and the solvent was evaporated under reduced pressure. The fraction eluted by reversed-phase preparative HPLC (Gilson Inc. UniPoint system, YMCODS column 30×75 mm, 0.1% TFA-containing acetonitrile-water (2:98 – 100:0)) was concentrated under reduced pressure, and crystallized from methanol. The obtained crystals were collected by filtration to give the object (97.5 mg). 1H-NMR (DMSO-d6) delta 1.66 (2H, ddd), 2.49 (2H, t), 3.78 (2H, t), 7.08-7.10 (2H, m), 7.18 (1H, ddd), 7.54 (1H, dt), 7.58-7.73 (4H, m), 7.85 (1H, t), 8.77 (1H, dd), 8.84 (1H, dd), 12.86 (1H, br s). In the same manner as in Example 4, the following compound was obtained using methyl 7-aminothieno[2,3-b]pyrazine-6-carboxylate and 3-(3,4-dihydro-1(2H)-quinolinylsulfonyl)aniline.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,111042-89-8, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1847541; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 111042-89-8 ,Some common heterocyclic compound, 111042-89-8, molecular formula is C9H8N2O2S, 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.

3-[3-(3,4-Dihydroquinolin-1(2H)-ylsulfonyl)phenyl]pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidin-2,4(1H,3H)-dione [Show Image] To a 0.75N solution (1.16 ml) of methyl 3-aminothieno[2,3-b]pyridine-2-carboxylate in dichloromethane, a 2.25N solution (1.12 ml) of triethylamine in dichloromethane was added, and then a 0.25N solution (1.36 ml) of triphosgene in dichloromethane was added dropwise on stirring to the mixture under nitrogen atmosphere at -78C. The cold bath was removed, the mixture was stirred for additional 20 min, and the reaction mixture was concentrated under reduced pressure. The residue was diluted with THF (4.2 ml). A solution of 3-(3,4-dihydro-1(2H)-quinolinylsulfonyl)aniline (0.25N) and DMAP (0.375N) in THF (1.12 ml) was added dropwise, and the mixture was stirred at room temperature for 25 hr. Insoluble triethylamine hydrochloride was filtrated, and the solvent was evaporated under reduced pressure. The fraction eluted by reversed-phase preparative HPLC (Gilson Inc. UniPoint system, YMCODS column 30×75 mm, 0.1% TFA-containing acetonitrile-water (2:98 – 100:0)) was concentrated under reduced pressure, and crystallized from methanol. The obtained crystals were collected by filtration to give the object (97.5 mg). 1H-NMR (DMSO-d6) delta 1.66 (2H, ddd), 2.49 (2H, t), 3.78 (2H, t), 7.08-7.10 (2H, m), 7.18 (1H, ddd), 7.54 (1H, dt), 7.58-7.73 (4H, m), 7.85 (1H, t), 8.77 (1H, dd), 8.84 (1H, dd), 12.86 (1H, br s). In the same manner as in Example 4, the following compound was obtained using methyl 7-aminothieno[2,3-b]pyrazine-6-carboxylate and 3-(3,4-dihydro-1(2H)-quinolinylsulfonyl)aniline.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,111042-89-8, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1847541; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 111042-89-8, Adding some certain compound to certain chemical reactions, such as: 111042-89-8, name is Methyl 3-aminothieno[2,3-b]pyridine-2-carboxylate,molecular formula is C9H8N2O2S, 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 111042-89-8.

EXAMPLE 1 3-(1-Piperazinyl)thieno[2,3-b]pyridine maleate A mixture of 3-aminothieno[2,3-b]pyridine-2-carboxylic acid methyl ester (8.00 g), piperazine (6.70 g), and N-methyl-2-pyrrolidinone (80 ml) was heated to 145 C. for 3 hr, under a nitrogen atmosphere. The solution was allowed to cool, diluted with water (400 ml), and extracted with ethyl acetate. The combined extracts were washed with water and brine dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to give 4.94 g (86.0%) of residual thieno[2,3-b]pyridine-3-amine.

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. 111042-89-8, Methyl 3-aminothieno[2,3-b]pyridine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoechst-Roussel Pharmaceuticals Incorporated; US5272148; (1993); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem