Ammonium Chloride → 2-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamide

HRID 2067614Notes

Reaction equation

HRID 2067614 reaction equation
ClC1C=CC2SC=C(C[N:10]3CCN(C4SC(C(O)=O)=C(C)N=4)C3=O)C=2C=1.[F:27][C:28]1[CH:49]=[CH:48][C:31]([CH2:32][N:33]2[CH2:37][CH2:36][N:35]([C:38]3[S:39][C:40]([C:44](O)=[O:45])=[C:41]([CH3:43])[N:42]=3)[C:34]2=[O:47])=[CH:30][CH:29]=1.[Cl-].[NH4+]>>[F:27][C:28]1[CH:49]=[CH:48][C:31]([CH2:32][N:33]2[CH2:37][CH2:36][N:35]([C:38]3[S:39][C:40]([C:44]([NH2:10])=[O:45])=[C:41]([CH3:43])[N:42]=3)[C:34]2=[O:47])=[CH:30][CH:29]=1

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 579197992-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 580315052-(3-((5-Chlorobenzo[b]thiophen-3-yl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 580314432-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamideYield 43%

Procedure

Following the procedure as described in Example 32, making variations as required to replace 2-(3-((5-chlorobenzo[b]thiophen-3-yl)methyl)-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 ammonium chloride, the title compound was obtained as a colorless solid in 43% yield: mp 201-203° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.38-7.31 (m, 4H), 7.23-7.17 (m, 2H), 4.42 (s, 2H), 3.99 (t, J=9.0 Hz, 2H), 3.45 (t, J=9.0 Hz, 2H), 2.46 (s, 3H); MS (ES+) m/z 335.1 (M+1).

Sources & evidence

ORD record
ord-2c0a3b5cd1a64362a10d491b27e163fd
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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