2-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamide → HCID 24983660, compound

HRID 1887285Notes

Reaction equation

HRID 1887285 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.[CH2:9]([NH:16][C:17]([C:19]1[S:23][C:22](Br)=[N:21][C:20]=1[CH3:25])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH2:9]([NH:16][C:17]([C:19]1[S:23][C:22]([N:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]2=[O:8])=[N:21][C:20]=1[CH3:25])=[O:18])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 579593962-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamideHCID 1785160645-chloropyridin-2-ol

Product 1

HCID 24983660HCID 24983660, compoundYield 39%

Procedure

Following the procedure as described in Example 3, making variations only as required to use 5-chloro-2-hydroxypyridine 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 39% yield: mp 173-174° C.; 1H NMR (300 MHz, CDCl3) δ 8.79 (d, J=2.4 Hz, 1H), 7.36-7.23 (m, 6H), 6.61 (d, J=9.9 Hz, 1H), 6.43 (s, 1H), 4.55 (d, J=5.4 Hz, 2H), 2.66 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 161.9, 158.8, 152.4, 152.0, 141.0, 131.7, 128.7, 128.5, 127.8, 127.6, 123.8, 121.9, 115.5, 44.1, 17.2; MS (ES+) m/z 360.1 (M+1), 362.1 (M+1).

Sources & evidence

ORD record
ord-5fc1b9ae91a5439d8286718a1895dff6
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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