3-Pyridinemethanamine → 2-(3-(4-fluorobenzyl)-2-oxotetrahydropyrimidin-1(2H)-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide

HRID 560844Notes

Reaction equation

HRID 560844 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:50]=[CH:49][C:31]([CH2:32][N:33]2[CH2:38][CH2:37][CH2:36][N:35]([C:39]3[S:40][C:41]([C:45](O)=[O:46])=[C:42]([CH3:44])[N:43]=3)[C:34]2=[O:48])=[CH:30][CH:29]=1.[N:51]1[CH:56]=[CH:55][CH:54]=[C:53]([CH2:57][NH2:58])[CH:52]=1>>[F:27][C:28]1[CH:50]=[CH:49][C:31]([CH2:32][N:33]2[CH2:38][CH2:37][CH2:36][N:35]([C:39]3[S:40][C:41]([C:45]([NH:58][CH2:57][C:53]4[CH:52]=[N:51][CH:56]=[CH:55][CH:54]=4)=[O:46])=[C:42]([CH3:44])[N:43]=3)[C:34]2=[O:48])=[CH:30][CH:29]=1

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 580316052-(3-(4-fluorobenzyl)-2-oxotetrahydropyrimidin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 594812532-(3-(4-fluorobenzyl)-2-oxotetrahydropyrimidin-1(2H)-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideYield 15%

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-oxotetrahydropyrimidin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid to react with pyridin-3-ylmethanamine, the title compound was obtained as a colorless solid in 15% yield: mp 48-50° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.60-8.54 (m, 2H), 7.70 (d, J=7.6 Hz, 1H), 7.31-7.25 (m, 3H), 7.04-6.99 (m, 2H), 6.05-6.01 (m, 1H), 4.59-4.57 (m, 4H), 4.17 (t, J=5.8 Hz, 2H), 3.32 (t, J=5.8 Hz, 2H), 2.62 (s, 3H), 2.11-2.04 (m, 2H); MS (ES+) m/z 440.2 (M+1).

Sources & evidence

ORD record
ord-47d62e02ca5f4ef6a31e48f88b84b948
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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