Downstream synthetic route of 1593-08-4

1593-08-4, As the paragraph descriping shows that 1593-08-4 is playing an increasingly important role.

1593-08-4, 2-Formylquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 68 This Example illustrates the preparation of 7-Methoxy-2,2-dimethyl-benzo[1,3]dioxole-5-carboxylic acid [(2S,3aS,7aS)-1-(octahydro-indol-2-yl)methyl]-quinoxalin-2-ylmethyl-amide. Experimental conditions analogous to example 1, from with 80 mg (0.51 mmol) of quinoxaline-2-carbaldehyde, 0.15 g (0.61 mmol) of (2S,3aS,7aS)-2-aminomethyl-octahydro-indole-1-carboxylic acid tert-butyl ester, 5 mL dichloromethane, and 0.16 g (0.77 mmol) of sodium triacetoxyborohydride. The benzoylation step was performed using 0.21 mL (1.53 mmol) of triethylamine and 124 mg (0.51 mmol) of 7-methoxy-2,2-dimethyl-benzo[1,3]dioxole-5-carbonyl chloride. After 4 hours the reaction mixture was purified using flash chromatography (ethyl acetate in hexane). The residue was dissolved in 3 mL of 10% trifluoroacetic acid in dichloromethane, and after 4 hours neutralized with aqueous sodium bicarbonate and purified using reverse phase HPLC, mobile phase with a gradient 10-70% acetonitrile in 60 min. The residue was dissolved in dichloromethane, washed with aqueous sodium bicarbonate, dried with anhydrous magnesium sulfate and evaporated under vacuum to yield 60 mg of pale yellow solid as a free base. LC-MSD, m/z for C29H34N4O4 [M+H]+: 503.6. 1H NMR (400 MHz, CDCl3/HCl): delta 1.2-1.9 (m, 15H), 2.3-2.5 (m, 2H), 3.6-3.7 (m, 1H), 3.8 (s, 3H), 4.0-4.2 (m, 2H), 4.2-4.4 (m, 1H), 5.5-5.9 (m, 2H), 6.7 (s, 1H), 7.0 (s, 1H), 8.0-8.1 (m, 2H), 8.3-8.4 (ms, 1H), 8.5-8.6 (m, 1H), 9.0 (bs, 1H), 10.4 (bs, 1H), 10.6 (bs, 1H).

1593-08-4, As the paragraph descriping shows that 1593-08-4 is playing an increasingly important role.

Reference£º
Patent; ChemoCentryx, Inc.; US2006/74071; (2006); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider