4-Benzyloxy-2(1H)-pyridone → HCID 24985617, compound

HRID 1887311Notes

Reaction equation

HRID 1887311 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:12][C:13](Br)=[CH:14][C:15]=1[CH3:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][NH:29][C:28](=[O:32])[CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:1]([NH:8][C:9]([C:11]1[S:12][C:13]([N:29]2[CH:30]=[CH:31][C:26]([O:25][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:27][C:28]2=[O:32])=[CH:14][C:15]=1[CH3:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 36077244-Benzyloxy-2(1H)-pyridoneHCID 68494779HCID 68494779, compound

Product 1

HCID 24985617HCID 24985617, compoundYield 49%

Procedure

Following the procedure as described in Example 8, making variations only as required to use N-benzyl-5-bromo-3-methylthiophene-2-carboxamide in place of N-benzyl-5-bromothiophene-3-carboxamide to react with 4-(benzyloxy)pyridin-2(1H)-one, the title compound was obtained as colorless solid in 49% yield: mp 153-154° C.; 1H NMR (300 MHz, CDCl3) δ 7.55 (d, J=7.9 Hz, 1H), 7.43-7.27 (m, 10H), 6.84 (s, 1H), 6.20-6.11 (m, 2H), 6.05 (d, J=2.7 Hz, 1H), 5.03 (s, 2H), 4.59 (d, J=5.7 Hz, 2H), 2.54 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 166.4, 162.5, 161.9, 139.2, 137.6, 134.2, 128.43, 128.40, 128.3, 127.5, 127.4, 127.2, 126.7, 121.8, 102.9, 97.8, 70.3, 43.6, 15.6; MS (ES+) m/z 431.3 (M+1).

Sources & evidence

ORD record
ord-6f518550763c4742a61eaaf7bb03f10f
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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