4-Benzyloxy-2(1H)-pyridone → HCID 57744498, compound

HRID 1887300Notes

Reaction equation

HRID 1887300 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[S:21][C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:19]([CH3:27])[CH:18]=1>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:17]2[S:21][C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:19]([CH3:27])[CH:18]=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 60052343Ethyl 5-bromo-3-methylthiophene-2-carboxylate

Product 1

HCID 57744498HCID 57744498, compoundYield 26%

Procedure

Following the procedure as described in Example 3, making variations only as required to use 4-(benzyloxy)pyridin-2(1H)-one in place of 4-aminopyridin-2(1H)-one to react with ethyl 5-bromo-3-methylthiophene-2-carboxylate in place of N-benzyl-2-bromo-4-methylthiazole-5-carboxamide, the title compound was obtained as a colorless solid in 26% yield: 1H NMR (300 MHz, CDCl3) δ 7.55 (d, J=7.8 Hz, 1H), 7.44-7.36 (m, 5H), 6.87 (s, 1H), 6.13 (dd, J=7.8, 2.7 Hz, 1H), 6.07 (d, J=2.7 Hz, 1H), 5.04 (s, 2H), 4.32 (q, J=7.1 Hz, 2H), 2.55 (s, 3H), 1.36 (t, J=7.1 Hz, 3H); MS (ES+) m/z 370.2 (M+1).

Sources & evidence

ORD record
ord-eddc934cccf749d49bc105fc2795fd18
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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