Category: 1477-49-2

Brief introduction of 1477-49-2

1477-49-2 3-Indoleglyoxylic Acid 73863, aindole-building-block compound, is more and more widely used in various fields.

1477-49-2, 3-Indoleglyoxylic Acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

9.2 6-(1H-indol-3-yl)-3-(3-piperidin-1-yl-propylamino)-4H-1,2,4-triazin-5-one A solution of 0.55 g of (1H-indol-3-yl)-oxo-acetic acid and 1.04 g of N-(3-piperidin-1-yl-propyl)-hydrazinecarboximidamide hydroiodide, prepared in stage 9.1, in 3.5 cm3 of water is placed in a reactor. After sealing the tube, the mixture is submitted to discontinuous microwave irradiation for 10 min so that the temperature of the mixture is maintained at 140 C. Then cool the reaction mixture to a temperature close to 20 C., add ethanol and evaporate to dryness under reduced pressure (2.7 kPa) to give a residue which is purified by flash chromatography on silica under argon pressure (50 kPa) [eluent: dichloromethane/methanol/ammonia 32% (90/10/1 by volume)]. After concentrating the fractions under reduced pressure (2.7 kPa), we get 35 mg of 6-(1H-indol-3-yl)-3-(3-piperidin-1-yl-propylamino)-4H-1,2,4-triazin-5-one in the form of a solid. Mass spectrum (ES): m/z=353 (MH+, base peak). 1H-NMR spectrum (300 MHz)-delta in ppm-in DMSO-d6: From 1.15 to 1.85 (m spread-out, 6H); 1.95 (m, 2H); from 2.80 to 3.55 (m spread-out, 8H); from 7.05 to 7.22 (m, 3H); 7.47 (d broad, J=8.0 Hz, 1H); 8.31 (d broad, J=8.0 Hz, 1H); 8.62 (d, J=2.5 Hz, 1H); from 8.95 to 9.15 (m spread-out, 1H); 11.45 (m broad, 1H); 12.3 (m spread-out, 1H)., 1477-49-2

1477-49-2 3-Indoleglyoxylic Acid 73863, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; AVENTIS PHARMA S.A.; US2008/96891; (2008); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

New learning discoveries about 1477-49-2

The synthetic route of 1477-49-2 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1477-49-2,3-Indoleglyoxylic Acid,as a common compound, the synthetic route is as follows.

The reagents used for each of the amide bond formation was amino core (4 mumol), carboxylic acid (4 mumol, 1 eq.), DIEA (5 mumol, 1.2 eq.) and HBTU (4.5 mumol, 1.1eq.). A stock of the amino core for synthesis of 102 members requires an amount in excess of 150 fold. Both the starting amino core and the carboxylic acids were prepared as a stock solution of DMSO in a concentration of 0.6 mmol/1500 muL and 4 mumol/10 muL, respectively. HBTU and DIEA were dissolved in DMSO as a concentration of 4.5 mumol/10 muL (V/V) and 5 mumol/10 muL (V/V), respectively. Each of the acid portion was firstly mixed with the solution of HBTU in a plastic tube for 30 sec, followed by the addition of a mixture of the solution of amino core (4 mumol, 10 muL) and DIEA (10 muL) in a total volume of 40 muL. All vials were shaken for 1 min ultrasonically for the subsequent series dilution., 1477-49-2

The synthetic route of 1477-49-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Su, Yuan-Hsiao; Chiang, Li-Wu; Jeng, Kee-Ching; Huang, Ho-Lien; Chen, Jenn-Tzong; Lin, Wuu-Jyh; Huang, Chia-Wen; Yu, Chung-Shan; Bioorganic and Medicinal Chemistry Letters; vol. 21; 5; (2011); p. 1320 – 1324;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Analyzing the synthesis route of 1477-49-2

1477-49-2, 1477-49-2 3-Indoleglyoxylic Acid 73863, aindole-building-block compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1477-49-2,3-Indoleglyoxylic Acid,as a common compound, the synthetic route is as follows.

General procedure: 1 equiv of arylglyoxylic acid 12a was dissolved in 2 ml NMP and 1.1 equiv of CDI were added. The mixture was stirredat rt for 1 h followed by addition of 1 equiv of a-ketoamine12b. After stirring at rt over night water was added slowly to precipitate diketoamide 12c which was filtered off and washed with methanol and diethylether. Alternatively, the diketoamide was extracted by ethylacetate and purified by Flash chromatography.

1477-49-2, 1477-49-2 3-Indoleglyoxylic Acid 73863, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Article; Johannes, Eugen; Horbert, Rebecca; Schlosser, Joachim; Schmidt, Dorian; Peifer, Christian; Tetrahedron Letters; vol. 54; 31; (2013); p. 4067 – 4072;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Analyzing the synthesis route of 1477-49-2

1477-49-2 3-Indoleglyoxylic Acid 73863, aindole-building-block compound, is more and more widely used in various.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1477-49-2,3-Indoleglyoxylic Acid,as a common compound, the synthetic route is as follows.

To a solution of 2-amino-5-aminomethyl-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester (209 mg, 0.51 mmol) in dry N,N-dimethylformamide (4 ml) was added 3-indole-glyoxylic acid (141 mg, 0.74 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, hydrochloride (152 mg, 0.76 mmol), and 1-hydroxy-benzotriazole (100 mg, 0.74 mmol). The mixture was stirred at room temperature for 16 hours, diluted with dichloromethane (100 ml) and washed with water (100 ml), brine (100 ml), dried (MgSO4), filtered, and concentrated in vacuo. The residue was subjected to flash chromatography using a mixture of ethyl acetate/hexanes (2:5) as eluent, which afforded 143 mg (40 %) of 2-amino-5-((2-(1H-indol-3-yl)-2-oxo-acetylamino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester as an oil. LC-MS Rt= 2.31 min, m/z: 574.9 [M+H]+. To a solution of 2-amino-5-((2-(1H-indol-3-yl)-2-oxo-acetylamino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester (143 mg, 0.25 mmol) in dichloromethane (5 ml) was added imidazol-1-yl-oxo-acetic acid tert-butyl ester (144 mg, 0.75 mmol) and the flask was purged with nitrogen. After 24 hours an additional portion of imidazol-1-yl-oxo-acetic acid tert-butyl ester (169 mg, 0.86 mmol) was added and the reaction mixture allowed stirred for an additional 24 hours. The mixture was then concentrated in vacuo. The residue was purified by flash chromatography using a mixture of ethyl acetate/hexanes (2:5) as eluent, which afforded 101 mg (58 %) of 2-(tert-butyoxyoxalyl-amino)-5-((2-(1H-indol-3-yl)-2-oxo-acetylamino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester as a oil. 1H-NMR (CDCl3) delta 9.23 (s, 1H), 9.07 (d, 1H, J = 3.6 Hz), 8.50 (d, 1H, J = 7.6 Hz), 8.15 (d, 1H, J = 4.0 Hz), 7.47 (d, 2H, J = 7.2 Hz), 7.38-7.27 (m, 6H), 6.89 (d, 2H, J = 8.8 Hz), 3.87-3.59 (m, 6H), 3.04 (dd, 2H, J = 23.6 Hz), 2.74 (dd, 2H, J = 22.4 Hz), 1.62 (s, 18H); LC-MS Rt= 2.49 min, m/z: 703 [M+H]+. 2-(tert-Butyoxyoxalyl-amino)-5-((2-(1H-indol-3-yl)-2-oxo-acetylamino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester (101 mg, 0.143 mmol) was dissolved in dry tetrahydrofuran (6 ml) and passed through a pipette, plugged with cotton containing Raney 2800 Nickel (0.38 g). The pipette was flushed with dry tetrahydrofuran (6 ml) and the filtrate was concentrated in vacuo. Pd on carbon (10%, 102 mg, source: Avocado) and formic acid (10% in methanol, 5 ml) were added to the flask containing 2-(tert-Butyoxyoxalyl-amino)-5-((2-(1H-indol-3-yl)-2-oxo-acetylamino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester. After stirring for 18 hours, the solution was filtered through a pad of celite and concentrated in vacuo. The residue was diluted in ethyl acetate, washed with saturated sodium bicarbonate (2 x 25 ml), brine (2 x 25 ml), dried (MgSO4), filtered and concentrated in vacuo. The residue was subjected to flash chromatography using a mixtureof 10% methanol/dichloromethane as eluent, which afforded 2-(tert-butyoxyoxalyl-amino)-5-((2-(1H-indol-3-yl)-2-oxo-acetylamino)methyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester. 1H-NMR (CDCl3) delta 9.23 (s, 1H), 9.07 (d, 1H, J= 3.6 Hz), 8.50 (d, 1H, J = 7.6 Hz), 8.15 (d, 1H, J = 4.0 Hz), 7.27 (s, 2H), 7.09 (d, 1H, J = 8.8 Hz), 6.81 (d, 1H, J = 8.8 Hz), 3.79 (s, 1H), 2.29 (s, 1H), 1.62-1.57 (m, 18H), 0.08 (s, 5H); LC-MS: Rt= 2.17 min, m/z: 583 [M+H]+. The above 2-(tert-butyoxyoxalyl-amino)-5-((2-(1H-indol-3-yl)-2-oxo-acetylamino)methyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester was dissolved in 50% trifluoroacetic acid/dichloromethane (3 ml) and stirred at room temperature for 18 hours. The solvent was removed in vacuo and residual trifluoroacetic acid was removed under reduced pressure affording 17.1 mg of the title compound as a solid trifluoroacetate. 1H-NMR (DMSO-d6) delta 12.28 (s, 2H), 9.26 (s, 1H), 9.13 (s, 1H), 8.83 (d, 1H, J= 2.8 Hz), 8.26 (d, 1H, J = 8.8 Hz), 7.55 (d, 1H, J = 4.8 Hz), 7.27 (d, 2H, J = 7.6 Hz), 4.42 (d, 1H, J = 15.2 Hz), 4.29 (d, 1H, J = 16.4 Hz), 3.76-3.22 (m, 4H, partially obscured by solvent), 2.91-2.834 (m, 1H), 1.23 (s, 1H); LC-MS: Rt= 0.99 min, m/z 471.4 [M+H]+., 1477-49-2

1477-49-2 3-Indoleglyoxylic Acid 73863, aindole-building-block compound, is more and more widely used in various.

Reference£º
Patent; NOVO NORDISK A/S; Ontogen Corporation; EP1214324; (2006); B1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles