Potassium Carbonate → HCID 86639657, compound

HRID 1426102Notes

Reaction equation

HRID 1426102 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:15])[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH3:14])[N:13]=2)=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[Cl:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=1>>[ClH:22].[CH3:31][O:30][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[CH2:23][O:15][C:4]1[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH3:14])[N:13]=2)=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 699943-Methoxybenzyl chlorideHCID 86631476HCID 86631476, compound

Product 1

HCID 86639657HCID 86639657, compoundYield 7.04%

Procedure

5-Bromo-2-(4-methylthiazol-2-ylamino)pyridin-3-ol (prepared according to Example 3, Step A; 0.100 g, 0.349 mmol), K2CO3 (0.109 g, 0.786 mmol), and 1-(chloromethyl)-3-methoxybenzene (0.070 g, 0.349 mmol) were reacted according to Example 3, Step B, to provide 3-(3-methoxybenzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride (0.010 g, 7.04% yield). 1H NMR (d6-DMSO) δ 7.98 (m, 1H), 7.65 (s, 1H), 7.32 (t, 1H), 7.18 (s, 1H), 7.13 (d, 1H), 6.92 (dd, 1H), 6.66 (s, 1H), 5.27 (s, 2H), 3.77 (s, 3H), 2.25 (s, 3H). Mass spectrum (apci) m/z=406.0 (M+H-HCl).

Sources & evidence

ORD record
ord-95f7ba52f1724252964a8fea735c3860
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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