Trifluoroacetic acid → 3-(3-fluoro-4-(pyrrolidin-1-ylmethyl)phenyl)-N-isobutylcyclobut-2-enecarboxamide trifluoroacetate salt

Participants

Reaction Steps

A solution of Example 20, 3-(3-Fluoro-4-pyrrolidin-1-ylmethyl-phenyl)-3-hydroxy-cyclobutanecarboxylic acid isobutyl-amide (3.71 g, 10.64 mmol) in trifluoroacetic acid (20 mL) and 1,2-dichloroethane (120 mL) was refluxed for 21 h and concentrated to give 8.6 g of crude 3-(3-fluoro-4-(pyrrolidin-1-ylmethyl)phenyl)-N-isobutylcyclobut-2-enecarboxamide trifluoroacetate salt and residual TFA as a dark red-brown oil. Diagnostic 1H NMR signals: (CDCl3) δ 7.48 (t, J=7.7 Hz, 1H), 7.23 (d, partially obscured by CHCl3 signal, 1H), 7.09 (dd, J=10.3, 1.5 Hz, 1H), 6.38 (d J=0.8 Hz, 1H), 4.33 (d, J=5.0 Hz, 1H), 3.77 (br s, 2H), 3.68 (d, J=4.6 Hz, 1H), 3.20-3.07 (m, 3 h), 2.98 (br s, 2H), 2.83 (dd, J=13.3, 1.7 Hz, 1H), 2.19-2.07 (m, 4H), 0.90 (d, J=7.1H, 6H).

Provenance & Evidence