2-(Chloromethyl)-5-(4-chlorophenyl)-1,3,4-oxadiazole → N-Benzyl-2-(4-((5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl)methoxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

HRID 1887338

Reaction equation

HRID 1887338 reaction equation
Cl[CH2:2][C:3]1[O:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[N:6][N:7]=1.[CH2:15]([NH:22][C:23]([C:25]1[S:29][C:28]([N:30]2[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][C:31]2=[O:37])=[N:27][C:26]=1[CH3:38])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[CH2:15]([NH:22][C:23]([C:25]1[S:29][C:28]([N:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:2][C:3]3[O:4][C:5]([C:8]4[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=4)=[N:6][N:7]=3)=[CH:32][C:31]2=[O:37])=[N:27][C:26]=1[CH3:38])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 12682462-(Chloromethyl)-5-(4-chlorophenyl)-1,3,4-oxadiazoleHCID 54742338N-benzyl-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

Product 1

HCID 57744479N-Benzyl-2-(4-((5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl)methoxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamideYield 32%

Procedure

Following the procedure as described in Example 21, making variation only as required to use 2-(chloromethyl)-5-(4-chlorophenyl)-1,3,4-oxadiazole 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 32% yield: 1H NMR (300 MHz, DMSO-d6) δ 8.80 (t, J=5.8 Hz, 1H), 8.65 (d, J=7.8 Hz, 1H), 8.0 (d, J=8.6 Hz, 2H), 7.66 (d, J=8.5 Hz, 2H), 7.32-7.19 (m, 5H), 6.46-6.39 (m, 2H), 5.60 (s, 2H), 4.38 (d, J=5.8 Hz, 2H), 2.54 (s, 3H); MS (ES+) m/z 534.1 (M+1).

Sources & evidence

ORD record
ord-8d844ab70f63484ea896d5497b521daa
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Linked notes

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