2-Pyrimidinemethanamine → 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyrimidin-2-ylmethyl)thiazole-5-carboxamide

HRID 560835Notes

Reaction equation

HRID 560835 reaction equation
ClC1C=CC2SC=C(CN3CCN(C4SC(C(O)=O)=C(C)N=4)C3=O)C=2C=1.[F:27][C:28]1[CH:49]=[CH:48][C:31]([CH2:32][N:33]2[CH2:37][CH2:36][N:35]([C:38]3[S:39][C:40]([C:44]([OH:46])=O)=[C:41]([CH3:43])[N:42]=3)[C:34]2=[O:47])=[CH:30][CH:29]=1.[N:50]1[CH:55]=[CH:54][CH:53]=[N:52][C:51]=1[CH2:56][NH2:57]>>[F:27][C:28]1[CH:29]=[CH:30][C:31]([CH2:32][N:33]2[CH2:37][CH2:36][N:35]([C:38]3[S:39][C:40]([C:44]([NH:57][CH2:56][C:51]4[N:52]=[CH:53][CH:54]=[CH:55][N:50]=4)=[O:46])=[C:41]([CH3:43])[N:42]=3)[C:34]2=[O:47])=[CH:48][CH:49]=1

Participants

4

Reactant 3

HCID 46580472-PyrimidinemethanamineHCID 579197992-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 580315052-(3-((5-Chlorobenzo[b]thiophen-3-yl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 594812422-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyrimidin-2-ylmethyl)thiazole-5-carboxamideYield 70%

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 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid to react with pyrimidin-2-ylmethanamine, the title compound was obtained as a colorless solid in 70% yield: mp 205-207° C. (dichloromethane/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 8.76 (d, J=4.8 Hz, 2H), 8.42-8.38 (m, 1H), 7.41-7.7.34 (m, 3H), 7.23-7.17 (m, 2H), 4.58 (d, J=5.7 Hz, 2H), 4.43 (s, 2H), 4.04-3.99 (m, 2H), 3.49-3.43 (m, 2H), 2.50 (s, 3H); MS (ES+) m/z 427.2 (M+1).

Sources & evidence

ORD record
ord-ec70f198e6344a9c904038d9e9b813fe
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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