20699-85-8 | Page 8 of 10 | Heterocyclic Building Blocks-Benzothiophene

Downstream synthetic route of 20699-85-8

20699-85-8, The synthetic route of 20699-85-8 has been constantly updated, and we look forward to future research findings.

20699-85-8, Methyl 5-aminobenzo[b]thiophene-2-carboxylate is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Compound 61 (300 mg, 1.448 mmol) was dissolved in DMF (4.83 mL). Mel (109 pL, 1.737 mmol) was added, followed by K2C03 (300 mg, 2.171 mmol) and the reaction was stirred at rt overnight. Water was added to the reaction mixture to precipitate the product. The resulting slurry was filtered to obtain a brown solid. The crude product was purified by silica gel chromatography (10% to 100% EtOAc/hexanes) to obtain compound 64 as an orange solid (95 mg, 0.434 mmol, 30% yield). UPLCMS = 1.32 min (2.5 min method). Mass observed (ESI+): 222.4 (M+H).

20699-85-8, The synthetic route of 20699-85-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; IMMUNOGEN, INC.; MILLER, Michael, Louis; SHIZUKA, Manami; CHARI, Ravi, V.J.; (312 pag.)WO2019/133652; (2019); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

Brief introduction of 20699-85-8

Big data shows that 20699-85-8 is playing an increasingly important role.

20699-85-8, Methyl 5-aminobenzo[b]thiophene-2-carboxylate is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Compound 5 A (100 mg, 0.241 mmol) and amine 12 (43.7 mg, 0.289 mmol) were dissolved in DMF (1.61 mL). EDC (69.2 mg, 0.361 mmol) was added to the solution at rt, followed by DMAP (14.70 mg, 0.120 mmol) and was stirred overnight. Water was added to the reaction mixture to precipitate the product. The resulting slurry was stirred for 15 min. The solution was filtered and the solid was dried under vacuum/N2 for 2 h to obtain compound 13 as an off white solid (127 mg, 0.231 mmol, 96% yield). LCMS = 6.408 min (8 min method). Mass observed (ESI+): 549.15 (M+H). 1H NMR (400 MHz, DMSO-76): d 1.31 (s, 6H), 1.46 (s, 9H), 2.45 (s, 3H), 3.48 (d, 7 = 6.3 Hz, 2H), 3.83 (s, 3H), 6.97 (s, 2H), 7.72 – 7.79 (m, 1H), 7.92 (d, 7 = 8.8 Hz, 1H), 8.11 (d, 7 = 3.7 Hz, 1H), 8.31 – 8.41 (m, 2H), 8.70 (t, 7 = 6.3 Hz, 1H), 9.14 (s, 1H), 9.94 (s, 1H)., 20699-85-8

Big data shows that 20699-85-8 is playing an increasingly important role.

Some tips on 20699-85-8

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.20699-85-8,Methyl 5-aminobenzo[b]thiophene-2-carboxylate,as a common compound, the synthetic route is as follows.

A mixture of 500 mg of methyl 5-aminobenzo[b]thiophene-2-carboxylate, 320 mg of acetic anhydride, 623 mgof diisopropylethylamine, and 10 ml of dichloromethane was stirred for 4 hours at room temperature. The reaction mixturewas washed with an aqueous saturated sodium hydrogen carbonate solution and saturated saline, dried over magnesiumsulfate, and concentrated under reduced pressure. The residues were subjected to silica gel column chromatography,thereby obtaining 449 mg of methyl 5-(acetylamino)benzo[b]thiophene-2-carboxylate., 20699-85-8

As the paragraph descriping shows that 20699-85-8 is playing an increasingly important role.

Reference£º
Patent; Sumitomo Chemical Company Limited; MUKUMOTO, Fujio; TAMAKI, Hiroaki; KUSAKA, Shintaro; IWAKOSHI, Mitsuhiko; EP2926660; (2015); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

Some tips on 20699-85-8

As the paragraph descriping shows that 20699-85-8 is playing an increasingly important role.

Compound 60 (29 mg, 0.118 mmol) and compound 61 (37 mg, 0.177 mmol) were dissolved in DMF (1.18 mL). EDC (34 mg, 0.177 mmol) was added to the reaction mixture, followed by DMAP (14 mg, 0.118 mmol). The reaction was stirred at rt for 2 h. The solution was diluted with water and EtOAc and the layers were separated. The organic layer was washed with sat’d NH4Cl, water (3x), dried over Na2S04, filtered and concentrated. The crude residue was purified by RPHPLC (Cl 8 column, ACN/H20) to obtain compound 62 as a solid (10 mg, 0.023 mmol, 20% yield). UPLCMS = 1.69 min (2.5 min method). Mass observed (ESI+): 436.3 (M+H)., 20699-85-8

As the paragraph descriping shows that 20699-85-8 is playing an increasingly important role.

Brief introduction of 20699-85-8

20699-85-8, Big data shows that 20699-85-8 is playing an increasingly important role.

20699-85-8, Methyl 5-aminobenzo[b]thiophene-2-carboxylate is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

] A mixture of 500 mg of methyl 5-aminobenzo[b] thiophene-2-carboxylate, 323 mg of acetic anhydride, 623 mg of diisopropylethylamine, and 10 ml of dichloromethane was stirred for 4 hours at room temperature. The reaction mixture was washed with an aqueous saturated sodium hydrogen carbonate solution and saturated saline, dried over magnesium sulfate, and concentrated under reduced pressure. The residues were subjected to silica gel colunm chromatography, thereby obtaining 449 mg of methyl 5-(acetylamino) benzo[b]thiophene-2-carboxylate (hereinafier, described as a ?compound 67 of the present invention?).12238] Compound 67 of the Present InventionHj2239] ?H-NMR (CDC13) oe: 8.22-8.21 (m, 1H), 7.99 (s, 1H), 7.78-7.76 (m, 1H), 7.44-7.40 (m, 2H), 3.94 (s, 3H), 2.22 (s, 3H).

20699-85-8, Big data shows that 20699-85-8 is playing an increasingly important role.

Reference£º
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; Mukumoto, Fujio; Tamaki, Hiroaki; Kusaka, Shintaro; Iwakoshi, Mitsuhiko; US2015/282482; (2015); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

Brief introduction of 20699-85-8

20699-85-8, Big data shows that 20699-85-8 is playing an increasingly important role.

20699-85-8, Methyl 5-aminobenzo[b]thiophene-2-carboxylate is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

20699-85-8, Big data shows that 20699-85-8 is playing an increasingly important role.

Downstream synthetic route of 20699-85-8

20699-85-8, The synthetic route of 20699-85-8 has been constantly updated, and we look forward to future research findings.

20699-85-8, Methyl 5-aminobenzo[b]thiophene-2-carboxylate is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 5-amino- benzo[b]thiophene-2-carboxylic acid methyl ester (989 mg, 4.79 mmol) in CH2CWTHF (5/5 mL) was added NMM (630 muL, 5.73 mmol) and chloroacetylchloride (415 muL, 5.25 mmol). After stirring 2.5 h, the mixture was diluted with EtOAc and H2O, and the solid was filtered yielding a pale-white solid, which was used without exp (MH+) 284.

20699-85-8, The synthetic route of 20699-85-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK & CO., INC.; ATON PHARMA, INC.; WO2006/115845; (2006); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

Brief introduction of 20699-85-8

Big data shows that 20699-85-8 is playing an increasingly important role.

20699-85-8, Methyl 5-aminobenzo[b]thiophene-2-carboxylate is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The freshly prepared above acid chloride (1 equiv.) in CH2CI2 was added to a solution of compound 6-Amino-benzo[b]thiophene-2-carboxylic acid methyl ester (1 equiv.) in CH2CI2 and DIEA (1.1 equiv.). Reaction mixture was stirred for 3 hours at rt resulting in an orange gel-like suspension. It was then filtered and the residue was washed extensively with MeOH and dried under vacuum, yielding the product 5-[2-(9H-Fluoren- theta-ylmethoxycarbonylaminoJ-S-phenyl-propionylaminol-benzotbJthiophene^-carboxylic acid methyl ester as white solid. Yield: 87%., 20699-85-8

Big data shows that 20699-85-8 is playing an increasingly important role.

Reference£º
Patent; S*BIO PTE LTD; WO2006/101454; (2006); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

New learning discoveries about 20699-85-8

20699-85-8, The synthetic route of 20699-85-8 has been constantly updated, and we look forward to future research findings.

To a mixture of compound 133 (508 mg, 2.106 mmol) and compound 61 (300 mg, 1.404 mmol) in DMF (7.021 mL) was added EDC (567 mg, 2.81 mmol) and DMAP (429 mg, 3.51 mmol) at rt. After stirring for 3 h, the reaction was diluted with EtOAc and then washed with water, sat?d aq. NaHC03 and brine. The organic layer was dried over MgS04, filtered and concentrated to obtain compound 138, which was used in the next step without purification (0.6 g, 100% yield). LCMS = 8.36 min (15 min method). Mass observed (EST): 429.0 (M-H).

20699-85-8, The synthetic route of 20699-85-8 has been constantly updated, and we look forward to future research findings.

New learning discoveries about 20699-85-8

20699-85-8, The synthetic route of 20699-85-8 has been constantly updated, and we look forward to future research findings.

A mixture of 200 mg of methyl 5-aminobenzo[b]thiophene-2-carboxylate, 456 mg of trifluoroacetic anhydride,205 mg of triethylamine, and 10 ml of tetrahydrofuran was stirred for 24 hours at room temperature. Tert-butyl methylether was added to the reaction mixture, and the residue was washed with water, 1 M hydrochloric acid, an aqueoussaturated sodium hydrogen carbonate solution, and saturated saline, dried over magnesium sulfate, and concentratedunder reduced pressure. The residues were subjected to silica gel column chromatography, thereby obtaining 260 mgof methyl 5-(trifluoroacetylamino)benzo[b]thiophene-2-carboxylate.

20699-85-8, The synthetic route of 20699-85-8 has been constantly updated, and we look forward to future research findings.