2-Aminothiazole → HCID 59732997, compound

HRID 559991Notes

Reaction equation

HRID 559991 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[CH:5]=1.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(=O)C1C=CC=CC=1OC1C=CC(F)=CC=1N.[CH3:42][O:43][C:44](=[O:60])[C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([O:51][C:52]2[CH:57]=[CH:56][C:55]([F:58])=[CH:54][C:53]=2[NH2:59])[CH:46]=1.[NH2:61][C:62]1[S:63][CH:64]=[CH:65][N:66]=1>>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[N+:20]([O-:22])=[O:21])[CH:5]=1.[CH3:42][O:43][C:44](=[O:60])[C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([O:51][C:52]2[CH:57]=[CH:56][C:55]([F:58])=[CH:54][C:53]=2[NH:59][C:23]([NH:61][C:62]2[S:63][CH:64]=[CH:65][N:66]=2)=[O:24])[CH:46]=1

Participants

7

Reactant 5

HCID 21552-AminothiazoleHCID 677672,5-DifluoronitrobenzeneHCID 88068Methyl 3-HydroxybenzoateHCID 26189662HCID 26189662, compoundHCID 66998608HCID 66998608, compound

Product 2

HCID 59732997HCID 59732997, compoundYield 75%HCID 66999048HCID 66999048, compoundYield 50%

Procedure

3-(4-Fluoro-2-nitro-phenoxy)-benzoic acid methyl ester (0.73 g, 50%) was prepared from 3-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 (0.37 g, 58%) following general procedure C. 3-[4-Fluoro-2-(3-thiazol-2-yl-ureido)-phenoxy]-benzoic acid methyl ester (145 mg, 75%) was prepared from 3-(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-be6cbcceb6394d35a73ed64ee88ed5a9
Source dataset
uspto-grants-2011_11
Patent number
US08063081B2

Reaction notes

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