4-Benzyloxy-2(1H)-pyridone → HCID 24985949, compound

HRID 1887327Notes

Reaction equation

HRID 1887327 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:17]1[N:18]([CH3:28])[C:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:20]([CH3:22])[N:21]=1>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:17]2[N:18]([CH3:28])[C:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:20]([CH3:22])[N:21]=2)[C:11](=[O:15])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 36077244-Benzyloxy-2(1H)-pyridoneHCID 13897513ethyl 2-bromo-1,4-dimethyl-1H-imidazole-5-carboxylate

Product 1

HCID 24985949HCID 24985949, compoundYield 24%

Procedure

Following the procedure as described in Example 12, making variations only as required to use 4-(benzyloxy)pyridin-2(1H)-one in place of 4-phenylpyridin-2-ol to react with ethyl 2-bromo-1,4-dimethyl-1H-imidazole-5-carboxylate in place of ethyl 2-bromo-4-methylthiazole-5-carboxylate at 125° C. for 64 hours, the title compound was obtained as a colorless solid in 24% yield: 1H NMR (300 MHz, CDCl3) δ 7.44-7.36 (m, 5H), 7.22 (d, J=7.7 Hz, 1H), 6.09 (dd, J=7.7, 2.5 Hz, 1H) 5.98 (d, J=2.5 Hz, 1H), 5.04 (s, 2H), 4.35 (q, J=7.1 Hz, 2H), 3.69 (s, 3H), 2.49 (s, 3H), 1.38 (t, J=7.1 Hz, 3H); MS (ES+) m/z 368.2 (M+1).

Sources & evidence

ORD record
ord-5ac54dfe750e4abd865099bf8120349b
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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