Hydrochloric Acid → (N-1-Azabicyclo[2.2.2]oct-3-yl)-8-chloro-5-methoxy-1,2,3,4-tetrahydrobenzo-1,4-diazine-6-carboxamide

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Reaction Conditions

Reaction Steps

The carboxylic acid of step 7 above (3.71 mmoles) is dissolved in CHCl3 (10 ml), combined with Et3N (3.71 mmoles), cooled to -23° C. and mixed with ethyl chloroformate (3.71 mmoles) for 30 minutes. Aminoquinuclidine (14.8 mmoles) and aqueous K2CO3 (1 ml) are added and the reaction mixture is stirred for 1 hour and diluted with H2O (10 ml). The organic layer is separated, washed with aqueous NaHCO3 (50 ml, sat'd) and H2O (3×50 ml), dried, evaporated and chromatographed with Ether:MeOH (5 g, 1:1) to give a brown oil which is dissolved in EtOH. Concentrated HCl is added to the solution precipitating a white solid which is filtered and recrystallized affording a white solid which NMR indicates is the desired product.

Provenance & Evidence