3-Pyridinemethanamine → 4-methyl-2-(2-oxo-3-(quinolin-8-ylmethyl)imidazolidin-1-yl)-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

HRID 2067598Notes

Reaction equation

HRID 2067598 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]=[CH:44][CH:45]=[C:46]4[C:51]=3[N:50]=[CH:49][CH:48]=[CH:47]4)[C:37]2=[O:52])[S:31][C:32]=1[C:33](O)=[O:34].[NH2:53][CH2:54][C:55]1[CH:56]=[N:57][CH:58]=[CH:59][CH:60]=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]=[CH:44][CH:45]=[C:46]4[C:51]=3[N:50]=[CH:49][CH:48]=[CH:47]4)[C:37]2=[O:52])[S:31][C:32]=1[C:33]([NH:53][CH2:54][C:55]1[CH:56]=[N:57][CH:58]=[CH:59][CH:60]=1)=[O:34]

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 580315052-(3-((5-Chlorobenzo[b]thiophen-3-yl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 58031530HCID 58031530, compound

Product 1

HCID 250969384-methyl-2-(2-oxo-3-(quinolin-8-ylmethyl)imidazolidin-1-yl)-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideYield 44%

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-(quinolin-8-ylmethyl)imidazolidin-1-yl)thiazole-5-carboxylic acid to react with 3-(aminomethyl)pyridine, the title compound was obtained as a colorless solid in 44% yield: mp 225-228° C. (methanol); 1H NMR (300 MHz, DMSO-d6) δ 8.98-8.96 (m, 1H), 8.59-8.53 (m, 2H), 8.46-8.39 (m, 2H), 7.96-7.93 (m, 1H), 7.72-7.70 (m, 2H), 7.63-7.58 (m, 2H), 7.38-7.33 (m, 1H), 5.09 (s, 2H), 4.40 (d, J=5.8 Hz, 2H), 4.07-4.01 (m, 2H), 3.63-3.58 (m, 2H), 2.48 (s, 3H); MS (ES+) m/z 459.3 (M+1).

Sources & evidence

ORD record
ord-ce88a7c0762740a8b0e4600802b8aca2
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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