4-(Chloromethyl)-2-isopropyl-1,3-thiazole → HCID 57744513, compound

HRID 1887344Notes

Reaction equation

HRID 1887344 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([CH:8]([CH3:10])[CH3:9])[S:6][CH:7]=1.[CH2:11]([NH:18][C:19]([C:21]1[S:25][C:24]([N:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][C:27]2=[O:33])=[N:23][C:22]=1[CH3:34])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:11]([NH:18][C:19]([C:21]1[S:25][C:24]([N:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:2][C:3]3[N:4]=[C:5]([CH:8]([CH3:10])[CH3:9])[S:6][CH:7]=3)=[CH:28][C:27]2=[O:33])=[N:23][C:22]=1[CH3:34])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 27631934-(Chloromethyl)-2-isopropyl-1,3-thiazoleHCID 54742338N-benzyl-2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

Product 1

HCID 57744513HCID 57744513, compoundYield 36%

Procedure

Following the procedure as described in Example 21, making variation only as required to use 4-(chloromethyl)-2-isopropylthiazole 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 36% yield: 1H NMR (300 MHz, CDCl3) δ 8.67 (d, J=8.1 Hz, 1H), 7.34-7.23 (m, 5H), 7.21 (s, 1H), 6.28-6.20 (m, 1H), 6.10-6.04 (m, 2H), 5.12 (s, 2H), 4.59 (d, J=5.6 Hz, 2H), 3.38-3.27 (m, 1H), 2.68 (s, 3H), 1.45-1.35 (m, 6H); MS (ES+) m/z 481.2 (M+1).

Sources & evidence

ORD record
ord-212be88cd1b34bb693e83d921fd6201b
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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