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

HRID 560833Notes

Reaction equation

HRID 560833 reaction equation
ClC1C=CC2SC=C(C[N:10]3[CH2:14][CH2:13][N:12]([C:15]4SC(C(O)=O)=[C:18]([CH3:20])[N:19]=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.N1C=CC(CN)=NC=1>>[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:10][CH2:14][C:13]4[CH:20]=[CH:18][N:19]=[CH:15][N:12]=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 12933348Pyrimidin-4-ylmethanamineHCID 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 594812132-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyrimidin-4-ylmethyl)thiazole-5-carboxamideYield 71%

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-4-ylmethanamine, the title compound was obtained as a colorless solid in 71% yield: mp 175-176° C.; 1H NMR (300 MHz, CDCl3) δ 9.18 (s, 1H), 8.69 (d, J=6.0 Hz, 1H), 7.35-7.25 (m, 3H), 7.07-7.02 (m, 2H), 6.94 (br s, 1H), 4.70 (d, J=6.0 Hz, 2H), 4.47 (s, 2H), 4.10 (t, J=9.0 Hz, 2H), 3.47 (t, J=9.0 Hz, 2H), 2.64 (s, 3H); MS (ES+) m/z 427.2 (M+1).

Sources & evidence

ORD record
ord-a77205a659b94d06a97cba82e7c82d4c
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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