Benzylamine → N-benzyl-4-methyl-2-(2-oxo-3-(pyridin-3-ylmethyl)imidazolidin-1-yl)thiazole-5-carboxamide

HRID 560828Notes

Reaction equation

HRID 560828 reaction equation
ClC1C=CC2SC=C(CN3CCN(C4SC(C(O)=O)=C(C)N=4)C3=O)C=2C=1.[CH3:27][C:28]1[N:29]=[C:30]([N:36]2[CH2:40][CH2:39][N:38]([CH2:41][C:42]3[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=3)[C:37]2=[O:48])[S:31][C:32]=1[C:33]([OH:35])=O.[CH2:49]([NH2:56])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>>[CH2:49]([NH:56][C:33]([C:32]1[S:31][C:30]([N:36]2[CH2:40][CH2:39][N:38]([CH2:41][C:42]3[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=3)[C:37]2=[O:48])=[N:29][C:28]=1[CH3:27])=[O:35])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 580315052-(3-((5-Chlorobenzo[b]thiophen-3-yl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 58031579HCID 58031579, compound

Product 1

HCID 59481282N-benzyl-4-methyl-2-(2-oxo-3-(pyridin-3-ylmethyl)imidazolidin-1-yl)thiazole-5-carboxamideYield 13%

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 4-methyl-2-(2-oxo-3-(pyridin-3-ylmethyl)imidazolidin-1-yl)thiazole-5-carboxylic acid to react with benzylamine, the title compound was obtained as a colorless solid in 13% yield: mp 110-113° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.58-8.56 (m, 2H), 7.67 (d, J=7.8 Hz, 1H), 7.33-7.28 (m, 6H), 6.02 (br s, 1H), 4.57 (d, J=5.6 Hz, 2H), 4.49 (s, 2H), 4.11-4.06 (m, 2H), 3.51-3.45 (m, 2H), 2.61 (s, 3H); MS (ES+) m/z 408.2 (M+1).

Sources & evidence

ORD record
ord-9cfff899fe664774942ceed190ef3029
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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