4-Bromo-3-methylisoxazol-5-amine → HCID 23445351, compound

HRID 2270732Notes

Reaction equation

HRID 2270732 reaction equation
Cl[S:2]([C:5]1[S:6][C:7]([C:10]2[S:11][C:12]([CH3:15])=[CH:13][CH:14]=2)=[CH:8][CH:9]=1)(=[O:4])=[O:3].[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:2]([C:5]1[S:6][C:7]([C:10]2[S:11][C:12]([CH3:15])=[CH:13][CH:14]=2)=[CH:8][CH:9]=1)(=[O:4])=[O:3]

Participants

3

Reactant 2

HCID 104875194-Bromo-3-methylisoxazol-5-amineHCID 22998372HCID 22998372, compound

Product 1

HCID 23445351HCID 23445351, compoundYield 90.4%

Procedure

N-(4-bromo-3-methyl-5-isoxazolyl)-5-(5-methyl-2-thienyl)thiophene-2-sulfonamide was prepared in the same manner as described in Example 2. Reaction of 2-chlorosulfonyl-5-(5-methyl-2-thienyl)thiophene (200 mg, 0.72 mmol) with 5-amino-4-bromo-3-methylisoxazole (127 mg, 0.72 mmol) yielded 273 mg (90%) of the crude sulfonamide. After passing through a small plug of silica gel, a portion of the product was further purified by preparative HPLC to give the pure sulfonamide as a white powder, m.p. 161-162° C.

Workup

  1. customN-(4-bromo-3-methyl-5-isoxazolyl)-5-(5-methyl-2-thienyl)thiophene-2-sulfonamide was prepared in the same manner

Sources & evidence

ORD record
ord-84c7abd7558844da83da27df327ea4e4
Source dataset
uspto-grants-2001_12
Patent number
US06331637B1

Reaction notes

Loading…