IN-INTO Into DT a NN-PRESSURE pressure NN-APPARATUS reactor VBD was OSCAR-CJ placed OSCAR-CM 5-bromo-N-(2,3-dimethoxybenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide -LRB- ( CD .1 NN-MASS g COMMA , CD .24 NN-AMOUNT mmol -RRB- ) COMMA , OSCAR-CM 4-(dimethylamino)-benzenethiol -LRB- ( CD .147 NN-MASS g COMMA , CD .96 NN-AMOUNT mmol -RRB- ) CC and OSCAR-CM triethylamine -LRB- ( CD .363 NN-MASS g COMMA , CD .5 NN-VOL mL COMMA , CD 3.59 NN-AMOUNT mmol -RRB- ) STOP . DT The NN-APPARATUS vessel VBD was VB-DEGASS purged IN-WITH with OSCAR-CM nitrogen NN-STATE gas COMMA , VB-APPARATUS sealed CC and VB-HEAT heated TO to CD 135 NN-TEMP °C IN-FOR for CD 18 NN-TIME hours COMMA , IN-AFTER after WDT which NN-TIMES time PRP it VBD was VB-COOL cooled CC and DT the OSCAR-CJ excess OSCAR-CM triethylamine VB-REMOVE removed IN-IN in NN-VACUUM vacuo STOP . DT The NN-CHEMENTITY residue VBD was VB-PARTITION partitioned IN between OSCAR-CM EtOAc DASH / OSCAR-CM water CC and VB-EXTRACT extracted STOP . DT The OSCAR-CJ combined OSCAR-CJ organic VB-EXTRACT extracts VBD were VB-WASH washed IN-WITH with OSCAR-CM brine COMMA , VB-DRY dried IN-OVER over OSCAR-CM Na2SO4 COMMA , VB-FILTER filtered CC and DT the NN-CHEMENTITY solvent VB-REMOVE removed STOP . DT The VB-YIELD resulting NN-STATE glass VBD was VBN triturated IN-WITH with OSCAR-CM diethyl OSCAR-CM ether CC and VB-FILTER filtered TO to OSCAR-CJ yield OSCAR-CM N-(2,3-dimethoxybenzyl)-5-{[4-(dimethylamino)phenyl]thio}-8-hydroxy-1,6-naphthyridine-7-carboxamide IN-AS as DT a NN-STATE solid STOP .