4-Bromo-3-methylisoxazol-5-amine → HCID 22998430, compound

HRID 1738558Notes

Reaction equation

HRID 1738558 reaction equation
Cl[S:2]([C:5]1[S:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)(=[O:4])=[O:3].[NH2:20][C:21]1[O:25][N:24]=[C:23]([CH3:26])[C:22]=1[Br:27]>>[Br:27][C:22]1[C:23]([CH3:26])=[N:24][O:25][C:21]=1[NH:20][S:2]([C:5]1[S:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)(=[O:4])=[O:3]

Participants

3

Reactant 2

HCID 104875194-Bromo-3-methylisoxazol-5-amineHCID 22998471HCID 22998471, compound

Product 1

HCID 22998430HCID 22998430, compoundYield 41.2%

Procedure

N-(4-bromo-3-methyl-5-isoxazolyl)-5-(4-methoxycarbonylphenyl)thiophene-2-sulfonamide was prepared in the same manner as described in Example 2 from 2-chlorosulfonyl-5-(4-methoxycarbonylphenyl)thiophene (646 mg, 2.04 mmol) and 5-amino-4-bromo-3-methylisoxazole (361 mg, 2.04 mmol). Purification by column chromatography using 10% MeOH/CHCl3 gave 384 mg of N-(4-bromo-3-methyl-5-isoxazolyl)-5-(4-methoxycarbonylphenyl)thiophene-2-sulfonamide as a brown oil (41% yield).

Workup

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

Sources & evidence

ORD record
ord-b7adc7dd0cd04498a9a07de2288c3e05
Source dataset
uspto-grants-1999_10
Patent number
US05962490

Reaction notes

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