2-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamide → N-Benzyl-2-(3-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

HRID 1887289Notes

Reaction equation

HRID 1887289 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([OH:15])=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([NH:23][C:24]([C:26]1[S:30][C:29](Br)=[N:28][C:27]=1[CH3:32])=[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[S:30][C:29]([N:11]2[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:10]2=[O:15])=[N:28][C:27]=1[CH3:32])=[O:25])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 579593962-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamideHCID 178517714HCID 178517714, compound

Product 1

HCID 24985273N-Benzyl-2-(3-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamideYield 7%

Procedure

Following the procedure as described in Example 3, making variations only as required to use 3-(benzyloxy)pyridin-2-ol 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 white solid in 7% yield: mp 198-201° C.; 1H NMR (300 MHz, CDCl3) δ 8.45 (dd, J=6.0, 3.0 Hz, 1H), 7.46-7.29 (m, 10H), 6.73 (d, J=6.0 Hz, 1H), 6.32 (t, J=6.0 Hz, 1H), 6.13 (br, 1H), 5.15 (s, 2H), 4.61 (d, J=6.0 Hz, 2H), 2.71 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 187.9, 162.1, 152.1, 148.9, 137.7, 135.5, 128.8, 128.7, 128.3, 127.8, 127.7, 127.3, 122.9, 114.8, 106.7, 106.7, 96.8, 71.1, 44.1, 17.3; MS (ES+) m/z 432.2 (M+1).

Sources & evidence

ORD record
ord-21c6b0fdb17b4c4e83e84d8c972dbeb3
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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