4-(Chloromethyl)-2-methyl-1,3-thiazole → HCID 57744467, compound

HRID 1887346Notes

Reaction equation

HRID 1887346 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([CH3:8])[S:6][CH:7]=1.[CH2:9]([NH:16][C:17]([C:19]1[S:23][C:22]([N:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][C:25]2=[O:31])=[N:21][C:20]=1[CH3:32])=[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:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:2][C:3]3[N:4]=[C:5]([CH3:8])[S:6][CH:7]=3)=[CH:26][C:25]2=[O:31])=[N:21][C:20]=1[CH3:32])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 7363414-(Chloromethyl)-2-methyl-1,3-thiazoleHCID 54742338N-benzyl-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

Product 1

HCID 57744467HCID 57744467, compoundYield 20%

Procedure

Following the procedure as described in Example 21, making variation only as required to use 4-(chloromethyl)-2-methylthiazole 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 20% yield: 1H NMR (300 MHz, CDCl3) δ 8.67 (d, J=8.1 Hz, 1H), 7.34-7.26 (m, 5H), 7.20 (s, 1H), 6.24 (dd, J=8.1, 2.7 Hz, 1H), 6.13-6.07 (m, 2H), 5.10 (s, 2H), 4.59 (d, J=5.6 Hz, 2H), 2.73 (s, 3H), 2.67 (s, 3H); MS (ES+) m/z 453.1 (M+1).

Sources & evidence

ORD record
ord-f5be91eb0d7942dbba56f147321fb1f7
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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