Benzylamine → 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-N-(4-fluorobenzyl)isonicotinamide

Participants

Reaction Steps

Following the procedure as described in Example 15, making variations as required to replace benzylamine with 4-fluorobenzylamine to react with methyl 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)isonicotinate, 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-N-(4-fluorobenzyl)isonicotinamide was obtained as a colorless solid in 77% yield: mp 150-151° C.; 1H NMR (300 MHz, CDCl3) δ 8.53 (s, 1H), 8.34 (d, J=5.4 Hz, 1H), 7.39 (d, J=5.4 Hz, 1H), 7.30-7.24 (m, 2H), 7.01-6.91 (m, 3H), 4.55 (d, J=5.7 Hz, 2H), 4.06 (t, J=8.1 Hz, 2H), 3.59 (t, J=8.1 Hz, 2H), 3.13 (d, J=7.2 Hz, 2H), 99-0.85 (m, 1H), 0.59-0.51 (m, 2H), 0.24-0.19 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 165.7, 163.9, 160.6, 156.9, 153.1, 148.0, 133.6, 133.6, 129.8, 129.7, 115.9, 115.7, 115.4, 108.9, 48.6, 43.4, 41.6, 41.5, 9.0, 3.4; MS (ES+) m/z 369.3 (M+1).

Provenance & Evidence