2-(Bromomethyl)pyridine hydrobromide → HCID 24983812, compound

HRID 1887308Notes

Reaction equation

HRID 1887308 reaction equation
Br.Br[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[CH2:10]([NH:17][C:18]([C:20]1[S:24][C:23]([N:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][C:26]2=[O:32])=[N:22][C:21]=1[CH3:33])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:10]([NH:17][C:18]([C:20]1[S:24][C:23]([N:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=3)=[CH:27][C:26]2=[O:32])=[N:22][C:21]=1[CH3:33])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 54742338N-benzyl-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

Product 1

HCID 24983812HCID 24983812, compoundYield 11%

Procedure

Following the procedure as described in Example 6, making variations only as required to use 2-(bromomethyl)pyridine hydrobromide in place of 3-(bromomethyl)pyridine hydrobromide to react with N-benzyl-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 11% yield: mp 202-205° C.; 1H NMR (300 MHz, CDCl3/CD3OD) δ 8.69 (m, 1H), 8.53 (m, 1H), 7.89-7.84 (m, 1H), 7.56-7.49 (m, 2H), 7.39-7.35 (m, 1H), 7.28-7.17 (m, 5H), 6.36-6.32 (m, 1H), 6.07 (d, J=2.7 Hz, 1H), 5.18 (s, 2H), 4.46 (s, 2H), 2.56 (s, 3H); 13C NMR (75 MHz, CDCl3/CD3OD) δ 170.1, 165.7, 164.9, 156.7, 156.3, 154.0, 150.6, 141.9, 140.9, 134.7, 131.1, 130.0, 129.8, 126.8, 126.0, 125.5, 106.6, 100.1, 72.6, 46.2, 19.4; MS (ES+) m/z 433.3 (M+1).

Sources & evidence

ORD record
ord-2a43b9557ac04cf396aee67261134be6
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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