Benzylamine → N-benzyl-2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)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 benzylamine, N-benzyl-2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)isonicotinamide was obtained as a colorless solid in 31% yield: mp 121-123° C.; 1H NMR (300 MHz, CDCl3) δ 8.54 (s, 1H), 8.36 (d, J=5.4 Hz, 1H), 7.40 (d, J=5.1 Hz, 1H), 7.32-7.24 (m, 5H), 6.73 (br s, 1H), 4.60 (d, J=6.0 Hz, 2H), 4.06 (t, J=8.1 Hz, 2H), 3.59 (t, J=8.1 Hz, 2H), 3.14 (d, J=6.9 Hz, 2H), 1.00-0.87 (m, 1H), 0.57-0.51 (m, 2H), 0.24-0.19 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 165.7, 156.9, 153.2, 148.2, 142.9, 137.7, 128.8, 128.0, 127.7, 115.9, 108.8, 48.6, 44.2, 41.6, 41.5, 31.0, 9.0, 3.4; MS (ES+) m/z 351.3 (M+1).

Provenance & Evidence