2-Aminothiazole → HCID 59732811, compound

HRID 1983383Notes

Reaction equation

HRID 1983383 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10].F[C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[N+:20]([O-:22])=[O:21].[CH3:23][O:24][C:25](=[O:41])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[O:32][C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:34]=1[NH2:40].[NH2:42][C:43]1[S:44][CH:45]=[CH:46][N:47]=1>>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[N+:20]([O-:22])=[O:21].[CH3:23][O:24][C:25](=[O:41])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[O:32][C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:34]=1[NH:40][C:3]([NH:42][C:43]1[S:44][CH:45]=[CH:46][N:47]=1)=[O:11]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 4133Methyl SalicylateHCID 677672,5-DifluoronitrobenzeneHCID 66998608HCID 66998608, compound2×

Product 2

HCID 59732811HCID 59732811, compoundYield 65%HCID 66999161HCID 66999161, compoundYield 55%

Procedure

2-(4-Fluoro-2-nitro-phenoxy)-benzoic acid methyl ester (0.81 g, 55%) was prepared from 2-hydroxy-benzoic acid methyl ester (0.84 g, 5.5 mmol) and 2,5-difluoro-1-nitro-benzene (0.80 g, 5.0 mmol) following the general procedure A. This was reduced to 2-(2-amino-4-fluoro-phenoxy)-benzoic acid methyl ester (0.43 g, 60%) following general procedure C. 2-[4-Fluoro-2-(3-thiazol-2-yl-ureido)-phenoxy]-benzoic acid methyl ester (125 mg, 65%) was prepared from 2-(2-amino-4-fluoro-phenoxy)-benzoic acid methyl ester (130 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-078b3c2f7d874b7887d21bb5afb78963
Source dataset
uspto-grants-2009_06
Patent number
US07541373B2

Reaction notes

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