Benzylamine → HCID 44553452, compound

HRID 714386Notes

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:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[CH2:23][CH2:22][N:21]1[C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][N:40]=1)[C:35]([O-])=[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:38]=[CH:39][N:40]=[C:32]([N:21]2[CH2:22][CH2:23][N:24]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[C:20]2=[O:19])[CH:33]=1

Participants

Reactant 3

HCID 7504Benzylamine

HCID 1235723,4-Difluorobenzylamine

HCID 86653053HCID 86653053, compound

Product 1

HCID 44553452HCID 44553452, compoundYield 61%

Procedure

Following the procedure as described in Example 15, making variations as required to replace benzylamine with 3,4-difluorobenzylamine to react with 2-(2-oxo-3-(pyridin-2-ylmethyl)imidazolidin-1-yl)isonicotinate, N-(3,4-difluorobenzyl)-2-(2-oxo-3-(pyridin-2-ylmethyl)imidazolidin-1-yl)isonicotinamide was obtained as a colorless solid in 61% yield: mp 143-145° C.; 1H NMR (300 MHz, CDCl3) δ 8.64-8.53 (m, 2H), 8.36-8.35 (m, 1H), 7.68-7.63 (m, 1H), 7.40-7.38 (m, 1H), 7.29-7.02 (m, 6H), 4.57-4.52 (m, 4H), 4.06 (t, J=8.1 Hz, 2H), 3.53 (t, J=8.1 Hz, 2H); 13C NMR (75 MHz, CDCl3) δ 165.8, 157.2, 156.3, 153.0, 149.5, 148.4, 142.5, 137.1, 134.9, 123.9, 122.7, 122.1, 117.6, 117.3, 117.0, 116.8, 116.0, 108.9, 49.5, 43.0, 41.8, 41.5; MS (ES+) m/z 423.9 (M+1).

Sources & evidence

ORD record: ord-508b2a013c1248a8a43f2e7e56373ba2
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187426B2

Reaction notes

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