4-Bromo-3-methylisoxazol-5-amine → HCID 23445226, compound

HRID 234454Notes

Reaction equation

HRID 234454 reaction equation
Cl[S:2]([C:5]1[S:6][C:7]([C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=2)=[CH:8][CH:9]=1)(=[O:4])=[O:3].[NH2:24][C:25]1[O:29][N:28]=[C:27]([CH3:30])[C:26]=1[Br:31]>CO.C(Cl)(Cl)Cl>[Br:31][C:26]1[C:27]([CH3:30])=[N:28][O:29][C:25]=1[NH:24][S:2]([C:5]1[S:6][C:7]([C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=2)=[CH:8][CH:9]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 104875194-Bromo-3-methylisoxazol-5-amineHCID 229983975-[3,5-Bis(trifluoromethyl)phenyl]-2-thiophenesulfonyl chloride

Product 1

HCID 23445226HCID 23445226, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

N-(4-bromo-3-methyl-5-isoxazolyl)-5-[3,5-bis(trifluoromethyl)phenyl]thiophene-2-sulfonamide was prepared in the same manner as in Example 2. Reaction of 2-chlorosulfonyl-5-[3,5-bis(trifluoromethyl)phenyl]thiophene (250 mg, 0.63 mmol) with 5-amino-4-bromo-3-methylisoxazole (118 mg, 0.67 mmol) yielded, after column chromatography using 5% MeOH/CHCl3, 115.2 mg N-(4-bromo-3-methyl-5-isoxazolyl)-5-[3,5-bis(trifluoromethyl)phenyl]thiophene-2-sulfonamide as a white powder (34% yield). A portion of this sample was further purified by preparative HPLC, m.p. 140° C.

Workup

  1. customN-(4-bromo-3-methyl-5-isoxazolyl)-5-[3,5-bis(trifluoromethyl)phenyl]thiophene-2-sulfonamide was prepared in the same manner as in Example 2
  2. customyielded

Sources & evidence

ORD record
ord-cf629e69d9314f58a89822e6bab1fd70
Source dataset
uspto-grants-1997_01
Patent number
US05594021

Reaction notes

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