4-Benzyloxy-2(1H)-pyridone → N-Benzyl-5-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-3-methylfuran-2-carboxamide

HRID 1887299Notes

Reaction equation

HRID 1887299 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.[CH2:16]([NH:23][C:24]([C:26]1[O:27][C:28](Br)=[CH:29][C:30]=1[CH3:31])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH2:16]([NH:23][C:24]([C:26]1[O:27][C:28]([N:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][C:11]2=[O:15])=[CH:29][C:30]=1[CH3:31])=[O:25])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 36077244-Benzyloxy-2(1H)-pyridoneHCID 47242031N-benzyl-5-bromo-3-methylfuran-2-carboxamide

Product 1

HCID 57744442N-Benzyl-5-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-3-methylfuran-2-carboxamideYield 22%

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 N-benzyl-5-bromo-3-methylfuran-2-carboxamide in place of N-benzyl-2-bromo-4-methylthiazole-5-carboxamide, the title compound was obtained as a colorless solid in 22% yield: mp 191-192° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.92 (t, J=6.2 Hz, 1H), 8.23 (d, J=7.9 Hz, 1H), 7.49-7.20 (m, 10H), 6.78 (s, 1H), 6.25 (dd, J=7.9, 2.7 Hz, 1H), 6.06 (d, J=2.7 Hz, 1H), 5.15 (s, 2H), 4.43 (d, J=6.2 Hz, 2H), 2.33 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 166.4, 160.7, 158.3, 143.7, 139.6, 137.1, 135.4, 134.5, 128.4, 128.3, 128.2, 128.0, 127.2, 126.7, 105.6, 101.8, 97.6, 69.9, 41.5, 11.0; MS (ES+) m/z 415.3 (M+1).

Sources & evidence

ORD record
ord-98e893c04c3d4191b7e41b63ab04a6cf
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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