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

HRID 560824Notes

Reaction equation

HRID 560824 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[N:43]=[CH:44][O:45][C:46]=3[C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:37]2=[O:53])[S:31][C:32]=1[C:33](O)=[O:34].[NH2:54][CH2:55][C:56]1[CH:57]=[N:58][CH:59]=[CH:60][CH:61]=1>>[CH3:27][C:28]1[N:29]=[C:30]([N:36]2[CH2:40][CH2:39][N:38]([CH2:41][C:42]3[N:43]=[CH:44][O:45][C:46]=3[C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:37]2=[O:53])[S:31][C:32]=1[C:33]([NH:54][CH2:55][C:56]1[CH:57]=[N:58][CH:59]=[CH:60][CH:61]=1)=[O:34]

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 580314604-Methyl-2-(2-oxo-3-((5-phenyloxazol-4-yl)methyl)imidazolidin-1-yl)thiazole-5-carboxylic acidHCID 580315052-(3-((5-Chlorobenzo[b]thiophen-3-yl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 594812864-methyl-2-(2-oxo-3-((5-phenyloxazol-4-yl)methyl)imidazolidin-1-yl)-N-(pyridin-3-ylmethyl)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-((5-phenyloxazol-4-yl)methyl)imidazolidin-1-yl)thiazole-5-carboxylic acid to react with 3-(aminomethyl)-pyridine, the title compound was obtained as a colorless solid in 13% yield: mp 78-81° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.59 (s, 1H), 8.54 (d, J=4.8 Hz, 1H), 7.89 (s, 1H), 7.72-7.69 (m, 3H), 7.50-7.36 (m, 3H), 7.30-7.27 (m, 1H), 6.04-6.00 (m, 1H), 4.68 (s, 2H), 4.58 (d, J=5.8 Hz, 2H), 4.11-4.05 (m, 2H), 3.73-3.67 (m, 2H), 2.62 (s, 3H); MS (ES+) m/z 475.2 (M+1).

Sources & evidence

ORD record
ord-9df52a5b4b5649ba9d78f25520826877
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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