2-Pyridone → HCID 24985271, compound

HRID 1887291Notes

Reaction equation

[NH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]1=[O:7].[CH2:8]([NH:15][C:16]([C:18]1[S:22][C:21](Br)=[N:20][C:19]=1[CH3:24])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH2:8]([NH:15][C:16]([C:18]1[S:22][C:21]([N:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]2=[O:7])=[N:20][C:19]=1[CH3:24])=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Reactant 2

HCID 88712-Pyridone

HCID 579593962-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamide

Product 1

HCID 24985271HCID 24985271, compoundYield 48%

Procedure

Following the procedure as described in Example 3, making variations only as required to use pyridin-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 colorless solid in 48% yield: mp 180-182° C. (hexane/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 8.83 (t, J=5.9 Hz, 1H), 8.71 (dd, J=7.3, 1.7 Hz, 1H), 7.65-7.59 (m, 1H), 7.37-7.18 (m, 5H), 6.74 (d, J=9.3 Hz, 1H), 6.60-6.55 (m, 1H), 4.39 (d, J=5.9 Hz, 2H), 2.56 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 167.9, 162.0, 161.6, 154.1, 150.2, 139.9, 132.6, 128.7, 127.7, 127.2, 123.6, 104.4, 98.0, 43.1, 17.5; (ES+) m/z 326.1 (M+1).

Sources & evidence

ORD record: ord-091960bea18d4d2489b1d25d78d99741
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

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