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

HRID 714385Notes

Reaction equation

C(N)C1C=CC=CC=1.[F:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[F:18])[CH2:13][NH2:14].[O:19]=[C:20]1[N:24]([CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:23][CH2:22][N:21]1[C:32]1[CH:33]=[C:34]([CH:39]=[CH:40][N:41]=1)[C:35](OC)=[O:36]>>[F:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[F:18])[CH2:13][NH:14][C:35](=[O:36])[C:34]1[CH:39]=[CH:40][N:41]=[C:32]([N:21]2[CH2:22][CH2:23][N:24]([CH2:25][C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[C:20]2=[O:19])[CH:33]=1

Participants

Reactant 3

HCID 7504Benzylamine

HCID 1235723,4-Difluorobenzylamine

HCID 58247896Methyl 2-(2-oxo-3-(pyridin-3-ylmethyl)imidazolidin-1-yl)isonicotinate

Product 1

HCID 44553451N-(3,4-difluorobenzyl)-2-(2-oxo-3-(pyridin-3-ylmethyl)imidazolidin-1-yl)isonicotinamideYield 59%

Procedure

Following the procedure as described in Example 15, making variations as required to replace benzylamine with 3,4-difluorobenzylamine to react with methyl 2-(2-oxo-3-(pyridin-3-ylmethyl)imidazolidin-1-yl)isonicotinate, N-(3,4-difluorobenzyl)-2-(2-oxo-3-(pyridin-3-ylmethyl)imidazolidin-1-yl)isonicotinamide was obtained as a colorless solid in 59% yield: mp 178-180° C.; 1H NMR (300 MHz, CDCl3) δ 8.63-8.53 (m, 3H), 8.36 (dd, J=5.4, 0.6 Hz, 1H), 7.64-7.60 (m, 1H), 7.39 (dd, J=5.1, 1.5 Hz, 1H), 7.31-7.26 (m, 1H), 7.17-7.03 (m, 4H), 4.61 (d, J=6.6 Hz, 2H), 4.46 (s, 2H), 4.05 (t, J=8.1 Hz, 2H), 3.39 (t, J=8.1 Hz, 2H); 13C NMR (75 MHz, CDCl3) δ 165.8, 157.0, 152.9, 149.5, 149.4, 148.5, 142.6, 135.8, 134.9, 131.9, 123.9, 123.8, 117.6, 117.4, 117.0, 116.8, 116.1, 108.9, 45.5, 43.1, 41.3, 41.2; MS (ES+) m/z 423.9 (M+1).

Sources & evidence

ORD record: ord-082728a3d3f54487a50519bf09e2d023
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187426B2

Reaction notes

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