Benzylamine → N-(4-fluorobenzyl)-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinamide

HRID 714372Notes

Reaction equation

HRID 714372 reaction equation
C(N)C1C=CC=CC=1.C(N)C.[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1.[F:21][C:22]1[CH:44]=[CH:43][C:25]([CH2:26][N:27]2[CH2:31][CH2:30][N:29]([C:32]3[CH:33]=[C:34]([CH:39]=[CH:40][N:41]=3)[C:35](OC)=[O:36])[C:28]2=[O:42])=[CH:24][CH:23]=1>>[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH:18][C:35](=[O:36])[C:34]2[CH:39]=[CH:40][N:41]=[C:32]([N:29]3[CH2:30][CH2:31][N:27]([CH2:26][C:25]4[CH:24]=[CH:23][C:22]([F:21])=[CH:44][CH:43]=4)[C:28]3=[O:42])[CH:33]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 58247772Methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinateHCID 670796634-Fluorobenzylamine ethanamine

Product 1

HCID 44553108N-(4-fluorobenzyl)-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinamideYield 50%

Procedure

Following the procedure as described in Example 15, making variations as required to replace benzylamine with 4-fluorobenzylamine ethanamine to react with methyl 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinate, N-(4-fluorobenzyl)-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinamide was obtained as a colorless solid in 50% yield: mp 173-175° C.; 1H NMR (300 MHz, CDCl3) δ 8.57 (s, 1H), 8.35 (d, J=5.1 Hz, 1H), 7.41-7.39 (m, 1H), 7.31-7.21 (m, 4H), 7.04-6.96 (m, 4H), 6.84 (br s, 1H), 4.57 (d, J=5.7 Hz, 2H), 4.40 (s, 2H), 4.03 (t, J=8.1 Hz, 2H), 3.36 (t, J=8.1 Hz, 2H); MS (ES+) m/z 423.2 (M+1).

Sources & evidence

ORD record
ord-52f892ea802141859bbbfbd34a5bac37
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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