4-Bromo-3-methylisoxazol-5-amine → HCID 23445513, compound

HRID 2270739Notes

Reaction equation

HRID 2270739 reaction equation
Cl[S:2]([C:5]1[S:6][C:7]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[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[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)(=[O:4])=[O:3].[C:10]1([C:7]2[S:6][C:5]([S:2]([NH2:20])(=[O:4])=[O:3])=[CH:9][CH:8]=2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1.[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[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 104875194-Bromo-3-methylisoxazol-5-amineHCID 22998377HCID 22998377, compound

Product 2

HCID 23445513HCID 23445513, compoundYield 67.1%HCID 86757679HCID 86757679, compound

Procedure

N-14-bromo-3-methyl-5-isoxazolyl)-5-(1-naphthyl)thiophene-sulfonamide N-(4-bromo-3-methyl-5-isoxazolyl)-5-(1-naphthyl)thiophene-sulfonamide was prepared in the same manner as described in Example 2. Reaction of 2-chlorosulfonyl-5-(1-naphthyl)thiophene (200 mg, 0.65 mmol) with 5-amino-4-bromo-3-methylisoxazole (0.65 mmol), after purification by column chromatography using 1% MeOH/CHCl3, gave 65.3 mg of pure N-(4-bromo-3-methyl-5-isoxazolyl)-5-(1-naphthyl)thiophene-sulfonamide as a brown solid, (22% yield, m.p. 118° C.).

Workup

  1. customafter purification by column chromatography

Sources & evidence

ORD record
ord-09f320a1d85a45a2b1afd45d2f8ea189
Source dataset
uspto-grants-2001_12
Patent number
US06331637B1

Reaction notes

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