Benzylamine → N-(4-fluorobenzyl)-2-(2-oxo-3-(pyridin-4-ylmethyl)imidazolidin-1-yl)isonicotinamide
Reaction equation
C(N)C1C=CC=CC=1.[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH2:15])=[CH:12][CH:11]=1.[O:18]=[C:19]1[N:23]([CH2:24][C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[CH2:22][CH2:21][N:20]1[C:31]1[CH:32]=[C:33]([CH:38]=[CH:39][N:40]=1)[C:34](OC)=[O:35]>>[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH:15][C:34](=[O:35])[C:33]2[CH:38]=[CH:39][N:40]=[C:31]([N:20]3[CH2:21][CH2:22][N:23]([CH2:24][C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)[C:19]3=[O:18])[CH:32]=2)=[CH:12][CH:11]=1Participants
4
Procedure
Following the procedure as described in Example 15, making variations as required to replace benzylamine with 4-fluorobenzylamine to react with methyl 2-(2-oxo-3-(pyridin-4-ylmethyl)imidazolidin-1-yl)isonicotinate, N-(4-fluorobenzyl)-2-(2-oxo-3-(pyridin-4-ylmethyl)imidazolidin-1-yl)isonicotinamide was obtained as a colorless solid in 48% yield: mp 161-163° C.; 1H NMR (300 MHz, CDCl3) δ 8.67-8.50 (m, 3H), 8.37 (d, J=5.1 Hz, 1H), 7.49-7.20 (m, 5H), 7.02-6.96 (m, 2H), 6.84 (br s, 1H), 4.57 (d, J=5.7 Hz, 2H), 4.45 (s, 2H), 4.09 (t, J=8.1 Hz, 2H), 3.42 (t, J=8.1 Hz, 2H); MS (ES+) m/z 405.8 (M+1).
Sources & evidence
- ORD record
- ord-ff31164026a14a8d82c01235b04512dd
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187426B2
Reaction notes
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