Benzylamine → N-(4-fluorobenzyl)-2-(2-oxo-3-(pyridin-2-ylmethyl)imidazolidin-1-yl)isonicotinamide

HRID 714383Notes

Reaction equation

HRID 714383 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][CH:28]=[CH:27][N: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][CH:28]=[CH:27][N:26]=4)[C:19]3=[O:18])[CH:32]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 673264-FluorobenzylamineHCID 58247804Methyl 2-(2-oxo-3-(pyridin-2-ylmethyl)imidazolidin-1-yl)isonicotinate

Product 1

HCID 44553449N-(4-fluorobenzyl)-2-(2-oxo-3-(pyridin-2-ylmethyl)imidazolidin-1-yl)isonicotinamideYield 52%

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-2-ylmethyl)imidazolidin-1-yl)isonicotinate, the title compound was obtained as a colorless solid in 52% yield: mp 141-142° C.; 1H NMR (300 MHz, CDCl3) δ 8.56-8.53 (m, 2H), 8.35 (d, J=4.8 Hz, 1H), 7.68-6.86 (m, 9H), 4.57-4.54 (m, 4H), 4.06 (t, J=7.9 Hz, 2H), 3.53 (t, J=8.0 Hz, 2H); MS (ES+) m/z 405.7 (M+1).

Sources & evidence

ORD record
ord-7788ef483da54426bd5b90073090c3cf
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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