4-Bromo-3-methylisoxazol-5-amine → HCID 23445342, compound

HRID 1738520Notes

Reaction equation

HRID 1738520 reaction equation
[NH2:1][C:2]1[O:6][N:5]=[C:4]([CH3:7])[C:3]=1[Br:8].[CH2:9]([C:17]1[CH:18]=[C:19]([S:22](Cl)(=[O:24])=[O:23])[S:20][CH:21]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[Br:8][C:3]1[C:4]([CH3:7])=[N:5][O:6][C:2]=1[NH:1][S:22]([C:19]1[S:20][CH:21]=[C:17]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:18]=1)(=[O:23])=[O:24]

Participants

3

Reactant 2

HCID 104875194-Bromo-3-methylisoxazol-5-amineHCID 23445548HCID 23445548, compound

Product 1

HCID 23445342HCID 23445342, compoundYield 32%

Procedure

N-(4-bromo-3-methyl-5-isoxazolyl)-4-(phenethyl)thiophene-2-sulfonamide was prepared in the same manner as described in Example 2 using 5-amino-4-bromo-3-methyl-isoxazole (132.75 mg, 0.75 mmole) and 4-(phenethyl)thiophene-2-sulfonyl chloride (Example 11 9D; 225.62 mg, 0.75 mmol). The product was purified by HPLC (5-95% acetonitrile with 0.1% TFA over 30 min.) to give N-(4-bromo-3-methyl-5-isoxazolyl)-4-(phenethyl)thiophene-2-sulfonamide as a brownish oil 72.3mg, 32% yield.

Workup

  1. customN-(4-bromo-3-methyl-5-isoxazolyl)-4-(phenethyl)thiophene-2-sulfonamide was prepared in the same manner
  2. customThe product was purified by HPLC (5-95% acetonitrile with 0.1% TFA over 30 min.)

Sources & evidence

ORD record
ord-937527f0550f4b39be889aadd143f2e3
Source dataset
uspto-grants-1999_10
Patent number
US05962490

Reaction notes

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