4-Benzyloxy-2(1H)-pyridone → 2-(4-(Benzyloxy)-2-oxopyridin-1(2H)-yl)-N-(3,4-difluorobenzyl)-4-methylthiazole-5-carboxamide

HRID 1887298Notes

Reaction equation

HRID 1887298 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:18][C:19]([C:23]([NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[C:29]([F:34])[CH:28]=2)=[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[S:18][C:19]([C:23]([NH:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[C:29]([F:34])[CH:28]=3)=[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 666311772-Bromo-N-(3,4-difluorobenzyl)-4-methylthiazole-5-carboxamide

Product 1

HCID 577444432-(4-(Benzyloxy)-2-oxopyridin-1(2H)-yl)-N-(3,4-difluorobenzyl)-4-methylthiazole-5-carboxamideYield 85%

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 2-bromo-N-(3,4-difluorobenzyl)-4-methylthiazole-5-carboxamide, the title compound was obtained as a colorless solid in 85% yield: mp 225-227° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.67 (d, J=7.9 Hz, 1H), 7.43-7.35 (m, 5H), 7.17-7.05 (m, 3H), 6.35-6.19 (m, 2H), 6.05 (s, 1H), 5.03 (s, 2H), 4.52 (s, 2H), 2.67 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 167.4, 162.3, 162.0, 153.5, 152.6, 152.1, 151.5, 148.8, 135.0, 134.5, 131.5, 128.8, 127.7, 123.7, 121.8, 117.6, 116.9, 104.1, 97.3, 70.8, 42.9, 17.3; MS (ES+) m/z 468.3 (M+1).

Sources & evidence

ORD record
ord-7aa9f103e3874490b1c1c87b5dc61acd
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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