2-(Bromomethyl)-1,3-benzothiazole → HCID 57744471, compound

HRID 1887343Notes

Reaction equation

HRID 1887343 reaction equation
Br[CH2:2][C:3]1[S:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH2:12]([NH:19][C:20]([C:22]1[S:26][C:25]([N:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][C:28]2=[O:34])=[N:24][C:23]=1[CH3:35])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[S:4]1[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=[C:3]1[CH2:2][O:33][C:30]1[CH:31]=[CH:32][N:27]([C:25]2[S:26][C:22]([C:20]([NH:19][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:21])=[C:23]([CH3:35])[N:24]=2)[C:28](=[O:34])[CH:29]=1

Participants

3

Reactant 2

HCID 27762582-(Bromomethyl)-1,3-benzothiazoleHCID 54742338N-benzyl-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

Product 1

HCID 57744471HCID 57744471, compoundYield 14%

Procedure

Following the procedure as described in Example 21, making variation only as required to use 2-(bromomethyl)benzo[d]thiazole 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 14% yield: 1H NMR (300 MHz, DMSO-d6) δ 8.79 (t, J=5.9 Hz, 1H), 8.66 (d, J=8.1 Hz, 1H), 8.13-8.11 (m, 1H), 8.03-8.00 (m, 1H), 7.55-7.42 (m, 2H), 7.34-7.18 (m, 5H), 6.48 (dd, J=8.1, 2.7 Hz, 1H), 6.34 (d, J=2.7 Hz, 1H), 5.68 (s, 2H), 4.38 (d, J=5.9 Hz, 2H), 2.54 (s, 3H); MS (ES+) m/z 489.1 (M+1).

Sources & evidence

ORD record
ord-62c7b143349f487b930e0a50b8d3b6ce
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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