Triethylamine → 7-(trans-3-Amino-4-methoxy-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride

Participants

Reaction Steps

0.19 g (0.0036 mole) of sodium methoxide was added to a suspension of 0.34 g (0.0018 mole) of trans-3-amino-4-methoxypyrrolidine dihydrochloride (prepared as described in Preparation 18) in 1.5 ml of dimethyl sulfoxide, and the mixture was stirred at room temperature for 30 minutes. 0.31 g (0.0009 mole) of a chelate (IV) of 1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid and boron difluoride (prepared as described in Preparation 7) were added to the resulting solution, followed by 0.27 g (0.0027 mole) of triethylamine. The mixture was then allowed to stand at room temperature overnight. At the end of this time, 50 ml of water were added to the mixture, and a chelate (V) separated out. This was collected by filtration to give yellow crystals. These were worked up in a similar manner to that described in Example 22, to give 0.22 g of 7-(trans-3-amino-4-methoxy-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-8-methoxy-1,4 -dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride as a fine yellow powder, melting at 192°-195° C.

Provenance & Evidence