2-Aminothiazole → N-[2-(2,3-Dimethoxyphenoxy)pyridin-3-yl]-N'-(thiazol-2-yl)urea

HRID 598974Notes

Reaction equation

HRID 598974 reaction equation
COC1C(OC)=CC=C[C:4]=1[OH:11].BrC1C([N+]([O-])=O)=CC=CN=1.[CH3:22][O:23][C:24]1[C:37]([O:38][CH3:39])=[CH:36][CH:35]=[CH:34][C:25]=1[O:26][C:27]1[C:32]([NH2:33])=[CH:31][CH:30]=[CH:29][N:28]=1.[NH2:40][C:41]1[S:42][CH:43]=[CH:44][N:45]=1>>[CH3:22][O:23][C:24]1[C:37]([O:38][CH3:39])=[CH:36][CH:35]=[CH:34][C:25]=1[O:26][C:27]1[C:32]([NH:33][C:4]([NH:40][C:41]2[S:42][CH:43]=[CH:44][N:45]=2)=[O:11])=[CH:31][CH:30]=[CH:29][N:28]=1

Participants

5

Reactant 4

HCID 21552-AminothiazoleHCID 788282,3-DimethoxyphenolHCID 5550542-Bromo-3-nitropyridineHCID 669989442-(2,3-Dimethoxyphenoxy)-3-aminopyridine2×

Product 1

HCID 59732822N-[2-(2,3-Dimethoxyphenoxy)pyridin-3-yl]-N'-(thiazol-2-yl)ureaYield 70%

Procedure

2-(2,3-Dimethoxy)phenoxy-3-nitropyridine (1.03 g, 75%) was prepared from 2,3-dimethoxyphenol (0.85 g, 5.5 mmol) and 2-bromo-3-nitropyridine (1.05 g, 5.0 mmol) following the general procedure A. This compound was reduced to 2-(2,3-dimethoxyphenoxy)-3-aminopyridine (0.57 g, 62%) following the general procedure B. N-[2-(2,3-Dimethoxyphenoxy)pyridin-3-yl]-N′-(thiazol-2-yl)urea (131 mg, 70%) was prepared from 2-(2,3-dimethoxyphenoxy)-3-aminopyridine (123 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-a46fc45eff854ca286e85841e3f604fa
Source dataset
uspto-grants-2011_03
Patent number
US07897628B2

Reaction notes

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