HCID 17407254, compound → N-Benzyl-4-methyl-2-(2-oxo-5-(phenylcarbamoyl)pyridin-1(2H)-yl)thiazole-5-carboxamide

HRID 1887296Notes

Reaction equation

HRID 1887296 reaction equation
[O:1]=[C:2]1[NH:7][CH:6]=[C:5]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])[CH:4]=[CH:3]1.[CH2:17]([NH:24][C:25]([C:27]1[S:31][C:30](Br)=[N:29][C:28]=1[CH3:33])=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:17]([NH:24][C:25]([C:27]1[S:31][C:30]([N:7]2[CH:6]=[C:5]([C:8](=[O:9])[NH:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:4]=[CH:3][C:2]2=[O:1])=[N:29][C:28]=1[CH3:33])=[O:26])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 17407254HCID 17407254, compoundHCID 579593962-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamide

Product 1

HCID 24985441N-Benzyl-4-methyl-2-(2-oxo-5-(phenylcarbamoyl)pyridin-1(2H)-yl)thiazole-5-carboxamideYield 31%

Procedure

Following the procedure as described in Example 3, making variations only as required to use 6-oxo-N-phenyl-1,6-dihydropyridine-3-carboxamide in place of 4-aminopyridin-2(1H)-one to react with N-benzyl-2-bromo-4-methylthiazole-5-carboxamide, the title compound was obtained as a colorless solid in 31% yield: mp 223-225° C. (hexane/ethyl acetate); 1H-NMR (300 MHz, DMSO-d6) δ 10.39 (s, 1H), 9.40 (d, J=2.5 Hz, 1H), 8.89 (t, J=5.9 Hz, 1H), 8.14 (dd, J=9.6, 2.5 Hz, 1H), 7.70-7.68 (m, 2H), 7.36-7.28 (m, 6H), 7.26-7.18 (m, 1H), 7.11-7.07 (m, 1H), 6.86 (d, J=9.6 Hz, 1H), 4.41 (d, J=5.9 Hz, 2H), 2.61 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 162.4, 161.6, 160.1, 153.5, 150.5, 139.7, 139.3, 139.1, 134.0, 129.1, 128.7, 127.7, 127.3, 125.3, 124.4, 121.0, 120.2, 116.2, 43.2, 17.5; (ES+) m/z 445.1 (M+1).

Sources & evidence

ORD record
ord-78b9eb59edf147a389834d8622db0dab
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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