2-(Aminomethyl)-5-methylpyrazine → 4-methyl-N-((5-methylpyrazin-2-yl)methyl)-2-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiazole-5-carboxamide

HRID 560664Notes

Reaction equation

HRID 560664 reaction equation
C(N1CCN(C2SC(C(O)=O)=C(C)N=2)C1=O)C1C=CC=CC=1.[CH3:23][C:24]1[N:25]=[C:26]([N:32]2[CH2:36][CH2:35][N:34]([CH2:37][C:38]3[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][CH:39]=3)[C:33]2=[O:48])[S:27][C:28]=1[C:29](O)=[O:30].[NH2:49][CH2:50][C:51]1[CH:56]=[N:55][C:54]([CH3:57])=[CH:53][N:52]=1>>[CH3:23][C:24]1[N:25]=[C:26]([N:32]2[CH2:36][CH2:35][N:34]([CH2:37][C:38]3[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:45])[F:46])=[CH:40][CH:39]=3)[C:33]2=[O:48])[S:27][C:28]=1[C:29]([NH:49][CH2:50][C:51]1[CH:56]=[N:55][C:54]([CH3:57])=[CH:53][N:52]=1)=[O:30]

Participants

4

Reactant 3

HCID 27564962-(Aminomethyl)-5-methylpyrazineHCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 579199574-Methyl-2-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiazole-5-carboxylic acid

Product 1

HCID 594811944-methyl-N-((5-methylpyrazin-2-yl)methyl)-2-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiazole-5-carboxamideYield 42%

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 4-methyl-2-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiazole-5-carboxylic acid to react with 2-(aminomethyl)-5-methylpyrazine, the title compound was obtained as a white powder in 42% yield: mp 172-173° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.49 (s, 1H), 8.36 (s, 1H), 7.63 (d, J=7.8 Hz, 2H), 7.42 (d, J=7.8 Hz, 2H), 6.77 (t, J=4.8 Hz, 1H), 4.68 (d, J=4.8 Hz, 2H), 4.59 (s, 2H), 4.11-4.05 (m, 2H), 3.49-3.43 (m, 2H), 2.59 (s, 3H), 2.47 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 162.5, 157.5, 155.5, 153.0, 152.6, 148.7, 143.4, 142.7, 139.7, 130.6, 130.2, 128.5, 125.9, 125.8, 122.1, 117.7, 47.6, 42.3, 42.0, 41.9, 21.2, 17.3; MS (ES+) m/z 491.2 (M+1).

Sources & evidence

ORD record
ord-2d1c098480004b66bf62ff8bdff71a2c
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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