Fumaric Acid → 5-(Phenylethynyl)-3-(1-methyl-2-pyrrolidinyl)pyridine fumarate

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Reaction Steps

The above-described pyridine derivative was converted into invention compound of Formula I by the addition of one equivalent of fumaric acid to a methanol (10 mL) solution of the free amine at 25° C. After 30 minutes the solvent was removed in vacuo and the residue pumped under high vacuum. Trituration with diethyl ether followed by recrystallization from isopropyl acetate afforded 5-(phenylethynyl)-3-(1-methyl-2-pyrrolidinyl)pyridine fumarate, (56%). M.p. 152°-154° C. (decomp., iPrOAc); 1H NMR (DMSO-d6, 300 MHz): δ 9.6-10.4 (bs, 1 H), 8.5-8.9 (bs, 1 H), 8.00 (s, 1 H), 7.60(m, 2 H), 7.46 (m, 3 H), 6.63 (s, 3 H), 3.51 (app. t, J=8 Hz, 1 H), 3.33 (app. t, J=8 Hz, 1 H), 2.51 (m, 1 H), 2.24 (s, 3 H), 2.19-2.32 (m, 1 H), 1.7-2.0 (m, 3 H).

Provenance & Evidence