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

HRID 2067553Notes

Reaction equation

HRID 2067553 reaction equation
ClCC1C=CC(C#N)=CC=1.Br[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1.[CH2:20]([NH:27][C:28]([C:30]1[S:34][C:33]([N:35]2[CH2:39][CH2:38][NH:37][C:36]2=[O:40])=[N:32][C:31]=1[CH3:41])=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH2:20]([NH:27][C:28]([C:30]1[S:34][C:33]([N:35]2[CH2:39][CH2:38][N:37]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)[C:36]2=[O:40])=[N:32][C:31]=1[CH3:41])=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 680073-Fluorobenzyl bromideHCID 701274-(Chloromethyl)benzonitrileHCID 59481185N-benzyl-4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxamide

Product 1

HCID 25096187N-benzyl-2-(3-(3-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamideYield 8%

Procedure

Following the procedure as described in Example 23, making variations as required to replace 4-(chloromethyl)benzonitrile with 1-(bromomethyl)-3-fluorobenzene to react with N-benzyl-4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxamide, the title compound was obtained as a colorless solid in 8% yield: mp 155-156° C. (ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.40-7.27 (m, 6H), 7.06-6.96 (m, 3H), 5.87 (t, J=5.7 Hz, 1H), 4.56 (d, J=5.7 Hz, 2H), 4.45 (s, 2H), 4.10-4.05 (m, 2H), 3.49-3.43 (m, 2H), 2.60 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 162.2, 157.8, 155.5, 151.4, 140.1, 136.7, 129.1, 128.7, 128.2, 127.9, 127.6, 127.1, 118.2, 47.3, 43.0, 42.4, 42.0, 17.5; MS (ES+) m/z 425.3 (M+1).

Sources & evidence

ORD record
ord-5f64eeaea73247cbbf6b56c3a6f64ed4
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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