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

HRID 2067604Notes

Reaction equation

HRID 2067604 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:47]=[CH:46][CH:45]=[CH:44][N:43]=3)[C:37]2=[O:48])[S:31][C:32]=1[C:33]([OH:35])=O.[NH2:49][CH2:50][C:51]1[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=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:47]=[CH:46][CH:45]=[CH:44][N:43]=3)[C:37]2=[O:48])[S:31][C:32]=1[C:33]([NH:49][CH2:50][C:51]1[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=1)=[O:35]

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 580315124-Methyl-2-(2-oxo-3-(pyridin-2-ylmethyl)imidazolidin-1-yl)thiazole-5-carboxylic acid

Product 1

HCID 250974404-methyl-2-(2-oxo-3-(pyridin-2-ylmethyl)imidazolidin-1-yl)-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideYield 12%

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-2-ylmethyl)imidazolidin-1-yl)thiazole-5-carboxylic acid to react with 3-(aminomethyl)pyridine, the title compound was obtained as a colorless solid in 12% yield: mp 58-61° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.56-8.48 (m, 3H), 7.69-7.64 (m, 2H), 7.31-7.18 (m, 3H), 6.21 (br s, 1H), 4.58 (s, 2H), 4.56 (d, J=6.0 Hz, 2H), 4.09 (t, J=9.0 Hz, 2H), 3.62 (t, J=9.0 Hz, 2H), 2.59 (s, 3H); MS (ES+) m/z 409.2 (M+1).

Sources & evidence

ORD record
ord-a06b9bfa6903436a935b9286fc8e7273
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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