4-(Bromomethyl)thiazole → HCID 178490656, compound

HRID 2196804Notes

Reaction equation

HRID 2196804 reaction equation
[Br:1][C:2]1[S:6][C:5]([NH:7][C:8](=[O:18])[C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[O:16][CH3:17])=[N:4][CH:3]=1.Br[CH2:20][C:21]1[N:22]=[CH:23][S:24][CH:25]=1>>[Br:1][C:2]1[S:6]/[C:5](=[N:7]\[C:8](=[O:18])[C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[O:16][CH3:17])/[N:4]([CH2:20][C:21]2[N:22]=[CH:23][S:24][CH:25]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 98989844-(Bromomethyl)thiazoleHCID 60654877N-(5-bromothiazol-2-yl)-5-chloro-2-methoxybenzamide

Product 1

HCID 178490656HCID 178490656, compoundYield 52%

Procedure

A mixture of Example 17A (1001 mg, 3.33 mmol) and commercially available 4-(bromomethyl)thiazole were processed using the method described for Example 16B to afford the title compound (660 mg, 52% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 3.78 (s, 3 H), 5.54 (s, 2 H), 7.12 (d, J=9.2 Hz, 1 H), 7.49 (dd, J=8.8, 2.7 Hz, 1 H), 7.69 (dd, J=15.9, 2.4 Hz, 2 H), 7.93 (s, 1 H), 9.10 (d, J=2.0 Hz, 1 H) MS (DCI) m/z 445 (M+H)+; Anal. Calculated for C15H11BrClN3O2S2: C, 40.51; H, 2.49; N, 9.45. Found: C, 40.85; H, 2.90; N, 9.62.

Sources & evidence

ORD record
ord-220460a9177a4554919d9a7dc42b92f4
Source dataset
uspto-grants-2012_12
Patent number
US08338467B2

Reaction notes

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