4-Benzyloxy-2(1H)-pyridone → 5-(4-(Benzyloxy)-2-oxopyridin-1(2H)-yl)-N-(4-fluorobenzyl)-3-methylthiophene-2-carboxamide

HRID 1887301Notes

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]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[O:23])=[C:19]([CH3:33])[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]([NH:24][CH2:25][C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)=[O:23])=[C:19]([CH3:33])[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

Reactant 2

HCID 36077244-Benzyloxy-2(1H)-pyridone

HCID 686162425-bromo-N-(4-fluorobenzyl)-3-methylthiophene-2-carboxamide

Product 1

HCID 577444945-(4-(Benzyloxy)-2-oxopyridin-1(2H)-yl)-N-(4-fluorobenzyl)-3-methylthiophene-2-carboxamideYield 28%

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 5-bromo-N-(4-fluorobenzyl)-3-methylthiophene-2-carboxamide in place of N-benzyl-2-bromo-4-methylthiazole-5-carboxamide, the title compound was obtained as a colorless solid in 28% yield: mp 175-177° C.; 1H NMR (300 MHz, CDCl3) δ 7.55 (d, J=7.8 Hz, 1H), 7.43-7.36 (m, 5H), 7.31 (dd, J=8.5, 5.6 Hz, 2H), 7.02 (dd, J=8.5, 8.5 Hz, 2H), 6.84 (s, 1H), 6.20 (t, J=5.4 Hz, 1H), 6.14 (dd, J=7.8, 2.4 Hz, 1H), 6.05 (d, J=2.4 Hz, 1H), 5.03 (s, 2H), 4.54 (d, J=5.4 Hz, 2H), 2.53 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 166.8, 162.9, 162.2, 139.8, 139.7, 134.7, 134.4, 133.8 (JC-F=3.3 Hz), 129.5 (JC-F=8.1 Hz), 128.8, 127.8, 126.8, 121.9, 115.6 (JC-F=21.4 Hz), 103.4, 98.1, 70.6, 43.2, 15.9; MS (ES+) m/z 449.3 (M+1).

Sources & evidence

ORD record: ord-90db5aa88e34476cacdea7f06120425c
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

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