4-Fluorobenzylamine → 2-(3-(3,4-difluorobenzyl)-2-oxoimidazolidin-1-yl)-N-(4-fluorobenzyl)isonicotinamide

HRID 714388Notes

Reaction equation

HRID 714388 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2CCN(C3C=C(C=CN=3)C(OC)=O)C2=O)=[CH:4][CH:3]=1.[F:25][C:26]1[CH:27]=[C:28]([CH:46]=[CH:47][C:48]=1[F:49])[CH2:29][N:30]1[CH2:34][CH2:33][N:32]([C:35]2[CH:36]=[C:37]([CH:42]=[CH:43][N:44]=2)[C:38](OC)=[O:39])[C:31]1=[O:45].FC1C=CC(CN)=CC=1>>[F:25][C:26]1[CH:27]=[C:28]([CH:46]=[CH:47][C:48]=1[F:49])[CH2:29][N:30]1[CH2:34][CH2:33][N:32]([C:35]2[CH:36]=[C:37]([CH:42]=[CH:43][N:44]=2)[C:38]([NH:7][CH2:6][C:5]2[CH:23]=[CH:24][C:2]([F:1])=[CH:3][CH:4]=2)=[O:39])[C:31]1=[O:45]

Participants

4

Reactant 3

HCID 673264-FluorobenzylamineHCID 58247772Methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinateHCID 58247785Methyl 2-(3-(3,4-difluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate

Product 1

HCID 445536132-(3-(3,4-difluorobenzyl)-2-oxoimidazolidin-1-yl)-N-(4-fluorobenzyl)isonicotinamideYield 40%

Procedure

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-(3,4-difluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate to react with 4-fluorobenzylamine, 2-(3-(3,4-difluorobenzyl)-2-oxoimidazolidin-1-yl)-N-(4-fluorobenzyl)isonicotinamide was obtained as a colorless solid in 40% yield: mp 165-167° C.; 1H NMR (300 MHz, CDCl3) δ 8.62 (s, 1H), 8.37 (dd, J=5.1, 0.6 Hz, 1H), 7.41 (dd, J=5.4, 1.5 Hz, 1H), 7.37-7.26 (m, 2H), 7.13-6.97 (m, 5H), 6.80 (br s, 1H), 4.57 (d, J=5.7 Hz, 2H), 4.39 (s, 2H), 4.05 (t, J=8.1 Hz, 2H), 3.38 (t, J=8.1 Hz, 2H); MS (ES+) m/z 441.1 (M+1).

Sources & evidence

ORD record
ord-ad4e9056017844d19fec940af54732df
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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