4-Bromo-3-methylisoxazol-5-amine → HCID 54522885, compound

HRID 234374Notes

Reaction equation

HRID 234374 reaction equation
[CH3:1][C:2]1[O:3][CH:4]=[CH:5][C:6]=1[C:7]1[S:8][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:10][CH:11]=1.[NH2:16][C:17]1[O:21][N:20]=[C:19]([CH3:22])[C:18]=1[Br:23]>>[Br:23][C:18]1[C:19]([CH3:22])=[N:20][O:21][C:17]=1[NH:16][S:12]([C:9]1[S:8][C:7]([C:6]2[CH:5]=[CH:4][O:3][C:2]=2[CH3:1])=[CH:11][CH:10]=1)(=[O:14])=[O:13]

Participants

3

Reactant 2

HCID 104875194-Bromo-3-methylisoxazol-5-amineHCID 54124877HCID 54124877, compound

Product 1

HCID 54522885HCID 54522885, compoundYield 53.1%

Procedure

N-(4-bromo-3-methyl-5-isoxazolyl)-5-(2-methyl-furanyl)thiophene-2-sulfonamide was prepared in the same manner as described in Example 2. Reaction of 2-(2-methylfuranyl)thiophene-5-sulfonyl chloride (55 mg, 0.21 mmol) with 5-amino-4-bromo-3-methyl isoxazole (41 mg, 0.21 mmol), after purification by column chromatography using 10% MeOH/CHCl3, gave 45 mg of the pure sulfonamide as a brown semisolid, 54% yield, m.p. 123°-124° C.

Workup

  1. customN-(4-bromo-3-methyl-5-isoxazolyl)-5-(2-methyl-furanyl)thiophene-2-sulfonamide was prepared in the same manner
  2. customafter purification by column chromatography

Sources & evidence

ORD record
ord-14e1c180d77041afa950ee8db7e3a6d8
Source dataset
uspto-grants-1997_01
Patent number
US05594021

Reaction notes

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