Dichloromethane → (4aR,7aS)-1-[(4-fluorophenyl)methyl]-4-hydroxy-3-(7-iodo-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-3-yl)-5,6,7,7a-tetrahydro-4aH-cyclopenta[b]pyridin-2-one

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of cis-2-(4-fluoro-benzylamino)-cyclopentanecarboxylic acid ethyl ester (prepared as described in Example 11, 1.33 g, 5 mmol) and (7-iodo-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid (2.20 g, 6.0 mmol) in anhydrous N,N-dimethylformamide (15 mL) under a nitrogen atmosphere, a 1.0 M solution of N,N′-dicyclohexylcarbodiimide solution in dichloromethane (6.5 mL, 6.5 mmol) was slowly added. After stirring for 1.5 h at 25° C., the mixture was diluted with ethyl acetate, washed with water and saturated aqueous brine solution, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo to afford the amide intermediate, which was used directly in the next step without further purification.

Provenance & Evidence