4-Pyridinemethanamine → 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-N-(pyridin-4-ylmethyl)isonicotinamide

Participants

Reaction Steps

Following the procedure as described in Example 15, making variations as required to replace methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate with methyl 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)isonicotinate to react with pyridin-4-ylmethanamine, 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-N-(pyridin-4-ylmethyl)isonicotinamide was obtained as a colorless solid in 60% yield: mp 160-162° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.7-8.52 (m, 3H), 8.37 (d, J=5.1 Hz, 1H), 7.39 (d, J=5.1 Hz, 1H), 7.31-7.15 (m, 3H), 4.60 (d, J=4.5 Hz, 2H), 4.06 (t, J=8.1 Hz, 2H), 3.59 (t, J=8.1 Hz, 2H), 3.13 (d, J=6.9 Hz, 2H), 0.99-0.91 (m, 1H), 0.60-0.49 (m, 2H), 0.29-0.15 (m, 2H); 13C NMR (75 MHz, DMSO-d6) δ 166.2, 156.9, 153.2, 149.8, 148.5, 147.3, 142.2, 122.5, 115.8, 108.8, 48.6, 42.8, 41.6, 41.5, 9.0, 3.4; MS (ES+) m/z 352.3 (M+1).

Provenance & Evidence