3-(Chloromethyl)-1,2,4-oxadiazole → HCID 57744493, compound

HRID 1887347Notes

Reaction equation

HRID 1887347 reaction equation
Cl[CH2:2][C:3]1[N:7]=[CH:6][O:5][N:4]=1.[CH2:8]([NH:15][C:16]([C:18]1[S:22][C:21]([N:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][C:24]2=[O:30])=[N:20][C:19]=1[CH3:31])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[O:5]1[CH:6]=[N:7][C:3]([CH2:2][O:29][C:26]2[CH:27]=[CH:28][N:23]([C:21]3[S:22][C:18]([C:16]([NH:15][CH2:8][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)=[O:17])=[C:19]([CH3:31])[N:20]=3)[C:24](=[O:30])[CH:25]=2)=[N:4]1

Participants

3

Reactant 2

HCID 27357653-(Chloromethyl)-1,2,4-oxadiazoleHCID 54742338N-benzyl-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

Product 1

HCID 57744493HCID 57744493, compoundYield 20%

Procedure

Following the procedure as described in Example 21, making variation only as required to use 3-(chloromethyl)-1,2,4-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 20% yield: 1H NMR (300 MHz, DMSO-d6) δ 8.81 (t, J=5.9 Hz, 1H), 8.66 (d, J=8.1 Hz, 1H), 7.36-7.17 (m, 6H), 6.42 (dd, J=8.1, 2.8 Hz, 1H), 6.33 (d, J=2.8 Hz, 1H), 5.26 (s, 2H), 4.38 (d, J=5.9 Hz, 2H), 2.55 (s, 3H); MS (ES+) m/z 424.1 (M+1).

Sources & evidence

ORD record
ord-ab1bcb5d27c74f34aac140fec57ba205
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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