Reference of 6973-09-7, A common heterocyclic compound, 6973-09-7, name is 5-Amino-2-methylbenzenesulfonamide, molecular formula is C7H10N2O2S, 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.
Example No.B.1.1 : ter*-Butyl-cis-4-((6-(4-methyl-3-sulf amoylphenylamino)- l/ -p r azolo [3,4- i/|pyrimidin-l-yl)methyl)cyclohexylcarbamate; A solution of ~er~-butyl-cw-4-((6-chloro-l//-pyrazolo[3,4-i/]pyrimidin-l- yl)methyl)cyclohexylcarbamate (1.66 g, 4.53 mmol, prepared using A from Preparation No.2 and ter^butyl-czs-(4-hydroxymethyl)cyclohexylcarbamate [AMRI]), 5-amino-2- methylbenzenesulfonamide (1.10 g, 5.89 mmol, Waterstone), and sodium teri-butoxide (1.306 g, 13.59 mmol) in 1,4-dioxane (15 mL) was stirred at ambient temperature for about 30 min. In a separate 10 mL nitrogen purged vial charged with Pd2(dibenzylideneacetone)3 (0.415 g, 0.453 mmol) and 2-di-~er~-butylphosphino-2′,4′,6′-triisopropylbiphenyl (0.789 g, 1.86 mmol) was added 1,4-dioxane (2 mL) followed by heating to about 80 ¡ãC for about 2 min. The mixture was subsequently cooled to ambient temperature. The catalyst solution was added to the reaction mixture at ambient temperature and the reaction mixture was heated to about 80 ¡ãC for about 16 h. The reaction mixture was cooled to ambient temperature then water (100 mL) and EtOAc (50 mL) were added and the organic layer was separated. The aqueous layer was further extracted with EtOAc (2 x 50 mL) and the combined organic extracts were dried over anhydrous MgSOt, filtered through a silica gel pad, and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography eluting with 50percent EtOAc in heptane to provide tert-butyl-cis-4-((6- (4-methyl-3-sulfamoylphenylamino)-lH-pyrazolo[3,4-d]pyrimidin-l- yljmethyljcyclohexylcarbamate (0.58 g, 25percento) as a light yellow solid. LC/MS (Table 2, Method a) R, = 1.38 min; MS m/z: 516 (M+H)+.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; ABBOTT LABORATORIES; WOLLER, Kevin R.; CURTIN, Michael L.; FRANK, Kristine E.; JOSEPHSOHN, Nathan S.; LI, Biqin C.; WISHART, Neil; WO2011/156698; (2011); A2;,
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