4-Bromo-3-methylisoxazol-5-amine → HCID 15435846, compound

HRID 232745Notes

Reaction equation

HRID 232745 reaction equation
[NH2:1][C:2]1[O:6][N:5]=[C:4]([CH3:7])[C:3]=1[Br:8].[CH:9]([C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH:22]=[CH:21][CH:20]=[C:19]2[S:23](Cl)(=[O:25])=[O:24])=[CH:14][CH:13]=1)([CH3:11])[CH3:10].[CH:27]([C:30]1[CH:35]=[CH:34][C:33]([N:36]2[CH:40]=[CH:39][C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:37]2)=[CH:32][CH:31]=1)([CH3:29])[CH3:28]>>[Br:8][C:3]1[C:4]([CH3:7])=[N:5][O:6][C:2]=1[NH:1][S:23]([C:19]1[N:18]([C:15]2[CH:16]=[CH:17][C:12]([CH:9]([CH3:11])[CH3:10])=[CH:13][CH:14]=2)[CH:22]=[CH:21][CH:20]=1)(=[O:24])=[O:25].[Br:8][C:3]1[C:4]([CH3:7])=[N:5][O:6][C:2]=1[NH:1][S:41]([C:38]1[CH:39]=[CH:40][N:36]([C:33]2[CH:34]=[CH:35][C:30]([CH:27]([CH3:29])[CH3:28])=[CH:31][CH:32]=2)[CH:37]=1)(=[O:42])=[O:43]

Participants

5

Reactant 3

HCID 104875194-Bromo-3-methylisoxazol-5-amineHCID 23445392HCID 23445392, compoundHCID 23445476HCID 23445476, compound

Product 2

HCID 15435846HCID 15435846, compoundHCID 23445584HCID 23445584, compound

Procedure

N-(4-Bromo-3-methyl-5-isoxazolyl) 1-(4'-isopropylphenyl)pyrrole-2-sulfonamide and N-(4-bromo-3-methyl-5-isoxazolyl) 1-(4'-isopropylphenyl)pyrrole-3-sulfonamide were prepared in the same manner as described in Example 2 from 5-amino-4-bromo-3-methylisoxazole and a mixture of 1-(4'-isopropylphenyl)pyrrole-2-sulfonyl chloride and 1-(4'-isopropylphenyl)pyrrole-3-sulfonyl chloride in 65% combined yield. The mixture was subjected to preparative HPLC to give N-(4-bromo-3-methyl-5-isoxazolyl) 1-(4'-isopropylphenyl)pyrrole-2-sulfonamide (retention time 22.85 min, 5% to 95% acetonitrile in water with 0.1% TFA over 30 min period, C18 analytical column) and N-(4-bromo-3-methyl-5-isoxazolyl) 1-(4'-isopropylphenyl)pyrrole-3-sulfonamide (retention time 24.56 min, 5% to 95% acetonitrile in water with 0.1% TFA over 30 min period, C18 analytical column) as oils.

Workup

  1. customN-(4-Bromo-3-methyl-5-isoxazolyl) 1-(4'-isopropylphenyl)pyrrole-2-sulfonamide and N-(4-bromo-3-methyl-5-isoxazolyl) 1-(4'-isopropylphenyl)pyrrole-3-sulfonamide were prepared in the same manner
  2. customcombined yield

Sources & evidence

ORD record
ord-fa82201c62bf48ff8055d5575a19f6f4
Source dataset
uspto-grants-1997_01
Patent number
US05591761

Reaction notes

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