2-Hydroxy-3-methylpyrazine → HCID 24983659, compound

HRID 1887283Notes

Reaction equation

HRID 1887283 reaction equation
[CH3:1][C:2]1[C:3](=[O:8])[NH:4][CH:5]=[CH:6][N:7]=1.[CH2:9]([NH:16][C:17]([C:19]1[S:23][C:22](Br)=[N:21][C:20]=1[CH3:25])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH2:9]([NH:16][C:17]([C:19]1[S:23][C:22]([N:4]2[CH:5]=[CH:6][N:7]=[C:2]([CH3:1])[C:3]2=[O:8])=[N:21][C:20]=1[CH3:25])=[O:18])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 882762-Hydroxy-3-methylpyrazineHCID 579593962-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamide

Product 1

HCID 24983659HCID 24983659, compoundYield 5%

Procedure

Following the procedure as described in Example 3, making variations only as required to use 3-methylpyrazin-2(1H)-one in place of 4-aminopyridin-2(1H)-one to react with N-benzyl-2-bromo-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 5% yield: mp 186-187° C.; 1H NMR (300 MHz, CDCl3) δ 8.44 (s, 1H), 7.45-7.25 (m, 6H), 6.12 (s, 1H), 4.59 (d, J=5.7 Hz, 2H), 2.69 (s, 3H), 2.55 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 161.6, 159.2, 153.4, 152.4, 152.0, 137.5, 128.8, 127.9, 127.8, 124.5, 123.5, 119.3, 44.2, 20.8, 17.3; MS (ES+) m/z 341.2 (M+1).

Sources & evidence

ORD record
ord-2560eb5a6f764ebb96770f75fc241d23
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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