2-Aminothiazole → HCID 59732699, compound

HRID 1983384Notes

Reaction equation

HRID 1983384 reaction equation
[OH:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.F[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24].[NH2:26][C:27]1[CH:46]=[C:45]([F:47])[CH:44]=[CH:43][C:28]=1[O:29][C:30]1[C:31]([O:41][CH3:42])=[C:32]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])[CH:33]=[CH:34][CH:35]=1.[NH2:48][C:49]1[S:50][CH:51]=[CH:52][N:53]=1>>[F:22][C:19]1[CH:20]=[CH:21][C:16]([O:1][C:2]2[C:3]([O:13][CH3:14])=[C:4]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=2)=[C:17]([N+:23]([O-:25])=[O:24])[CH:18]=1.[F:47][C:45]1[CH:44]=[CH:43][C:28]([O:29][C:30]2[C:31]([O:41][CH3:42])=[C:32]([NH:36][S:37]([CH3:40])(=[O:38])=[O:39])[CH:33]=[CH:34][CH:35]=2)=[C:27]([NH:26][C:2]([NH:48][C:49]2[S:50][CH:51]=[CH:52][N:53]=2)=[O:1])[CH:46]=1

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 677672,5-DifluoronitrobenzeneHCID 66999128HCID 66999128, compoundHCID 66999168HCID 66999168, compound2×

Product 2

HCID 59732699HCID 59732699, compoundYield 64%HCID 66999041HCID 66999041, compoundYield 48%

Procedure

N-[3-(4-Fluoro-2-nitro-phenoxy)-2-methoxy-phenyl]-methanesulfonamide (0.86 g, 48%) was prepared from N-(3-hydroxy-2-methoxy-phenyl)-methanesulfonamide (1.2 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 N-[3-(2-amino-4-fluoro-phenoxy)-2-methoxy-phenyl]-methanesulfonamide (0.51 g, 70%) following general procedure C. N-{3-[4-Fluoro-2-(3-thiazol-2-yl-ureido)-phenoxy]-2-methoxy-phenyl}-methanesulfonamide (144 mg, 64%) was prepared from N-[3-(2-amino-4-fluoro-phenoxy)-2-methoxy-phenyl]-methanesulfonamide (123 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-7e60407c741842619a1596ff55e5b6fe
Source dataset
uspto-grants-2009_06
Patent number
US07541373B2

Reaction notes

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