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

HRID 560659Notes

Reaction equation

HRID 560659 reaction equation
C(N1CCN(C2SC(C(O)=O)=C(C)N=2)C1=O)C1C=CC=CC=1.[Cl:23][C:24]1[CH:45]=[CH:44][C:27]([CH2:28][N:29]2[CH2:33][CH2:32][N:31]([C:34]3[S:35][C:36]([C:40](O)=[O:41])=[C:37]([CH3:39])[N:38]=3)[C:30]2=[O:43])=[CH:26][CH:25]=1.[NH2:46][CH2:47][C:48]1[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=1>>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:28][N:29]2[CH2:33][CH2:32][N:31]([C:34]3[S:35][C:36]([C:40]([NH:46][CH2:47][C:48]4[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=4)=[O:41])=[C:37]([CH3:39])[N:38]=3)[C:30]2=[O:43])=[CH:44][CH:45]=1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 58031555HCID 58031555, compound

Product 1

HCID 594812242-(3-(4-chlorobenzyl)-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideYield 32%

Procedure

Following the procedure as describe in Example 9, making variations as required to replace 2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with 2-(3-(4-chlorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid to react with 3-(aminomethyl)pyridine, the title compound was obtained as a white powder in 32% yield: mp 178-179° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.58 (s, 1H), 8.48 (s, 1H), 7.68 (d, J=7.8 Hz, 1H), 7.30-7.16 (m, 5H), 6.42 (t, J=5.7 Hz, 1H), 4.56 (d, J=5.7 Hz, 2H), 4.40 (s, 2H), 4.09-3.97 (m, 2H), 3.44-3.39 (m, 2H), 2.57 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 162.6, 157.3, 155.4, 153.6, 149.0, 148.5, 135.9, 134.0, 133.9, 129.6, 129.0, 123.7, 117.0, 47.3, 42.0, 41.7, 41.3, 17.2: MS (ES+) m/z 442.3 (M+1), 444.3 (M+1).

Sources & evidence

ORD record
ord-afbb8c9a9ede4861b802ee49736564b1
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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