Benzylamine → N-benzyl-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamide

HRID 560652Notes

Reaction equation

HRID 560652 reaction equation
[CH2:1]([N:8]1CCN(C2SC(C(O)=O)=C(C)N=2)C1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:23][C:24]1[CH:45]=[CH:44][C:27]([CH2:28][N:29]2[CH2:33][CH2:32][N:31]([C:34]3[S:35][C:36]([C:40](O)=[O:41])=[C:37]([CH3:39])[N:38]=3)[C:30]2=[O:43])=[CH:26][CH:25]=1.C(N)C1C=CC=CC=1>>[CH2:1]([NH:8][C:40]([C:36]1[S:35][C:34]([N:31]2[CH2:32][CH2:33][N:29]([CH2:28][C:27]3[CH:26]=[CH:25][C:24]([F:23])=[CH:45][CH:44]=3)[C:30]2=[O:43])=[N:38][C:37]=1[CH3:39])=[O:41])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 579197992-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 25095150N-benzyl-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamideYield 16%

Procedure

Following the procedure as describe in Example 9, making variations as required to replace 2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid to react with benzylamine, the title compound was obtained as a white powder in 16% yield: mp 192-193° C.; 1H NMR (300 MHz, CDCl3) δ 7.37-7.21 (m, 7H), 7.04-6.98 (m, 2H), 5.95 (s, 1H), 4.54 (d, J=5.7 Hz, 2H), 4.41 (s, 2H), 4.03 (t, J=8.1 Hz, 2H), 3.42 (t, J=8.1 Hz, 2H), 2.58 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 164.1, 162.3, 157.2, 155.3, 152.9, 137.9, 133.8, 131.3, 129.9, 128.7, 127.7, 117.3, 115.9, 47.2, 44.0, 42.0, 41.6, 17.2; MS (ES+) m/z 425.2 (M+1).

Sources & evidence

ORD record
ord-f4087037467d4bdd89795f64f7cf559d
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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