(2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-thiophen-2-yl-methanone → cyclopropyl-(2-methyl-4-thiophen-2-yl-6,7-dihydro-5H-cyclopenta[4.5]thieno[2,3-b]pyridin-3-yl)-methanone

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 60 mg (0.24 mmol) (2-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-thiophen-2-yl-methanone) (the preparation of which is described in example 2) in 2 ml acetic acid was added 40 mg (0.32 mmol) of 1-cyclopropyl-butane-1,3-dione and one drop of sulfuric acid. The mixture was then stirred at 100° C. for 10 minutes in a microwave and then concentrated in vacuo. Preparative HPLC (30% CH3CN/H20) afforded 15 mg (19%) cyclopropyl-(2-methyl-4-thiophen-2-yl-6,7-dihydro-5H-cyclopenta[4.5]thieno[2,3-b]pyridin-3-yl)-methanone as a light brown oil. ES-MS m/e (%): 340 (M+H+, 100).

Provenance & Evidence