2-Chloro-5-(chloromethyl)pyridine → HCID 57744456, compound

HRID 1887345Notes

Reaction equation

HRID 1887345 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=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][CH2:8][C:5]3[CH:4]=[N:3][C:2]([Cl:1])=[CH:7][CH:6]=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 1554792-Chloro-5-(chloromethyl)pyridineHCID 54742338N-benzyl-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

Product 1

HCID 57744456HCID 57744456, compoundYield 73%

Procedure

Following the procedure as described in Example 21, making variation only as required to use 2-chloro-5-(chloromethyl)pyridine in place of 2-(chloromethyl)-5-phenyl-1,3,4-oxadiazole to react with N-benzyl-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide, the title compound was obtained as a colorless solid in 73% yield: 1H NMR (300 MHz, DMSO-d6) δ 8.79 (t, J=5.9 Hz, 1H), 8.62 (d, J=8.1 Hz, 1H), 8.51 (d, J=2.4 Hz, 1H), 7.95 (dd, J=8.3, 2.5 Hz, 1H), 7.57-7.54 (m, 1H), 7.35-7.16 (m, 5H), 6.39 (dd, J=8.1, 2.7 Hz, 1H), 6.26 (d, J=2.7 Hz, 1H), 5.22 (s, 2H), 4.38 (d, J=5.9 Hz, 2H), 2.54 (s, 3H); MS (ES+) m/z 467.0 (M+1).

Sources & evidence

ORD record
ord-0229b5c6ff474018930802457fb60a43
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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