3-(Bromomethyl)-5-methylisoxazole → HCID 57744460, compound

HRID 1887341Notes

Reaction equation

HRID 1887341 reaction equation
Br[CH2:2][C:3]1[CH:7]=[C:6]([CH3:8])[O:5][N:4]=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[CH:7]=[C:6]([CH3:8])[O:5][N:4]=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 27763043-(Bromomethyl)-5-methylisoxazoleHCID 54742338N-benzyl-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

Product 1

HCID 57744460HCID 57744460, compoundYield 47%

Procedure

Following the procedure as described in Example 21, making variation only as required to use 3-(bromomethyl)-5-methylisoxazole 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 47% yield: 1H NMR (300 MHz, DMSO-d6) δ 8.79 (t, J=5.9 Hz, 1H), 8.62 (d, J=8.1 Hz, 1H), 7.35-7.18 (m, 5H), 6.38-6.35 (m, 2H), 6.26 (d, J=2.6 Hz, 1H), 5.22 (s, 2H), 4.38 (d, J=5.9 Hz, 2H), 2.54 (s, 3H), 2.38 (s, 3H); MS (ES+) m/z 437.2 (M+1).

Sources & evidence

ORD record
ord-f6f22d6663fc438da49002d92f3949bb
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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