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

HRID 560823Notes

Reaction equation

HRID 560823 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[C:43]([CH3:53])=[N:44][O:45][C:46]=3[C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:37]2=[O:54])[S:31][C:32]=1[C:33](O)=[O:34].[NH2:55][CH2:56][C:57]1[CH:58]=[N:59][CH:60]=[CH:61][CH:62]=1>>[CH3:27][C:28]1[N:29]=[C:30]([N:36]2[CH2:40][CH2:39][N:38]([CH2:41][C:42]3[C:43]([CH3:53])=[N:44][O:45][C:46]=3[C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:37]2=[O:54])[S:31][C:32]=1[C:33]([NH:55][CH2:56][C:57]1[CH:58]=[N:59][CH:60]=[CH:61][CH:62]=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 580315224-Methyl-2-(3-((3-methyl-5-phenylisoxazol-4-yl)methyl)-2-oxoimidazolidin-1-yl)thiazole-5-carboxylic acid

Product 1

HCID 594812654-methyl-2-(3-((3-methyl-5-phenylisoxazol-4-yl)methyl)-2-oxoimidazolidin-1-yl)-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideYield 50%

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-(3-((3-methyl-5-phenylisoxazol-4-yl)methyl)-2-oxoimidazolidin-1-yl)thiazole-5-carboxylic acid to react with 3-(aminomethyl)pyridine, the title compound was obtained as a colorless solid in 50% yield: mp 109-111° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.59 (s, 1H), 8.53-8.51 (m, 1H), 7.74-7.70 (m, 1H), 7.58-7.54 (m, 2H), 7.47-7.42 (m, 3H), 7.32-7.28 (m, 1H), 6.13 (br s, 1H), 4.58 (d, J=5.8 Hz, 2H), 4.45 (s, 2H), 3.91-3.85 (m, 2H), 3.19-3.14 (m, 2H), 2.58 (s, 3H), 2.51 (s, 3H); MS (ES+) m/z 489.3 (M+1).

Sources & evidence

ORD record
ord-5aa8b4058be54b1d85ceb1acffc05e8b
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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