4-Bromo-3-methylisoxazol-5-amine → HCID 23445455, compound

HRID 234414Notes

Reaction equation

HRID 234414 reaction equation
Cl[S:2]([C:5]1[S:6][C:7]([CH2:10][O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][CH:9]=1)(=[O:4])=[O:3].[NH2:19][C:20]1[O:24][N:23]=[C:22]([CH3:25])[C:21]=1[Br:26]>>[Br:26][C:21]1[C:22]([CH3:25])=[N:23][O:24][C:20]=1[NH:19][S:2]([C:5]1[S:6][C:7]([CH2:10][O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][CH:9]=1)(=[O:4])=[O:3]

Participants

3

Reactant 2

HCID 104875194-Bromo-3-methylisoxazol-5-amineHCID 23445479HCID 23445479, compound

Product 1

HCID 23445455HCID 23445455, compoundYield 31.2%

Procedure

N-(4-bromo-3-methyl-5-isoxazolyl)-5-(benzyloxymethyl)thiophene-2-sulfonamide was prepared as described in Example 2 from 2-chlorosulfonyl-5-(benzyloxymethyl)thiophene (520 mg, 1.72 mmol) and 5-amino-4-bromo-3-methyl isoxazole (319 mg, 1.8 mmol). Purification by column chromatography using 10% MeOH/CHCl3) gave 238 mg of pure N-(4-bromo-3-methyl-5-isoxazolyl)-5-(benzyloxymethyl)thiophene-2-sulfonamide as brown semisolid (31% yield, m.p. 92° C.).

Workup

  1. customN-(4-bromo-3-methyl-5-isoxazolyl)-5-(benzyloxymethyl)thiophene-2-sulfonamide was prepared
  2. customPurification by column chromatography

Sources & evidence

ORD record
ord-7c4b1175c1204217bd3197ccfe04da01
Source dataset
uspto-grants-1997_01
Patent number
US05594021

Reaction notes

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