4-Fluorobenzylamine → 2-(3-((4-(difluoromethyl)phenyl)-difluoromethyl)-2-oxoimidazolidin-1-yl)-N-(4-fluorobenzyl)isonicotinamide

HRID 714389Notes

Reaction equation

HRID 714389 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][CH:26]([F:52])[C:27]1[CH:32]=[CH:31][C:30]([C:33]([F:51])([F:50])[N:34]2[CH2:38][CH2:37][N:36]([C:39]3[CH:40]=[C:41]([CH:46]=[CH:47][N:48]=3)[C:42]([O:44]C)=O)[C:35]2=[O:49])=[CH:29][CH:28]=1.FC1C=CC(CN)=CC=1>>[F:52][CH:26]([F:25])[C:27]1[CH:28]=[CH:29][C:30]([C:33]([F:50])([F:51])[N:34]2[CH2:38][CH2:37][N:36]([C:39]3[CH:40]=[C:41]([CH:46]=[CH:47][N:48]=3)[C:42]([NH:7][CH2:6][C:5]3[CH:23]=[CH:24][C:2]([F:1])=[CH:3][CH:4]=3)=[O:44])[C:35]2=[O:49])=[CH:31][CH:32]=1

Participants

4

Reactant 3

HCID 673264-FluorobenzylamineHCID 58247772Methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinateHCID 58247774Methyl 2-(3-((4-(difluoromethyl)phenyl)difluoromethyl)-2-oxoimidazolidin-1-yl)isonicotinate

Product 1

HCID 445536142-(3-((4-(difluoromethyl)phenyl)-difluoromethyl)-2-oxoimidazolidin-1-yl)-N-(4-fluorobenzyl)isonicotinamideYield 41%

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-((4-(difluoromethyl)phenyl)difluoromethyl)-2-oxoimidazolidin-1-yl)isonicotinate to react with 4-fluorobenzylamine, 2-(3-((4-(difluoromethyl)phenyl)-difluoromethyl)-2-oxoimidazolidin-1-yl)-N-(4-fluorobenzyl)isonicotinamide was obtained as a colorless solid in 41% yield: mp 173-175° C.; 1H NMR (300 MHz, CDCl3) δ 8.40 (d, J=5.1 Hz, 1H), 8.25 (s, 1H), 7.73 (d, J=8.1 Hz, 2H), 7.60 (d, J=7.8 Hz, 2H), 7.47 (dd, J=5.1, 0.9 Hz, 1H), 7.25-7.21 (m, 2H), 6.99-6.90 (m, 2H), 6.86-6.42 (m, 2H), 4.50 (d, J=5.7 Hz, 2H), 4.18 (t, J=7.8 Hz, 2H), 3.89 (t, J=7.8 Hz, 2H); MS (ES+) m/z 490.9 (M+1).

Sources & evidence

ORD record
ord-31b3c7823a4a4901b4778f26db1bc915
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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