Sodium hydride → N-(4-chloro-3-methyl-5-isoxazolyl)thieno[2,3-b]pyridine-3-sulfonamide

HRID 2268985Notes

Reaction equation

HRID 2268985 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:5]([CH3:10])=[N:6][O:7][C:8]=1[NH2:9].[S:11]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[C:13]([S:20](Cl)(=[O:22])=[O:21])=[CH:12]1>C1COCC1>[Cl:3][C:4]1[C:5]([CH3:10])=[N:6][O:7][C:8]=1[NH:9][S:20]([C:13]1[C:14]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[S:11][CH:12]=1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 105828224-Chloro-3-methyl-1,2-oxazol-5-amineHCID 18614041Thieno[2,3-b]pyridine-3-sulfonyl chloride

Product 1

HCID 12044906N-(4-chloro-3-methyl-5-isoxazolyl)thieno[2,3-b]pyridine-3-sulfonamideYield 96.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(4-chloro-3-methyl-5-isoxazolyl)thieno[2,3-b]pyridine-3-sulfonamide was prepared by the method of Example 1(C) using NaH (0.16 g, 6.8 mmoles), THF (10 ml), 4-chloro-3-methyl-5-aminoisoxazole (0.36 g, 2.7 mmoles) and thieno[2,3-b]pyridine-3-sulfonyl chloride (0.70 g, 3.0 mmoles) to provide 0.86 g (96%) of the title compound as a tan solid. Recrystallization of 56 mg from EtOAc/hexanes provided 43 mg of a light tan solid, m.p. 176-177° C.

Workup

  1. customN-(4-chloro-3-methyl-5-isoxazolyl)thieno[2,3-b]pyridine-3-sulfonamide was prepared by the method of Example 1(C)

Sources & evidence

ORD record
ord-c3a718b832974702a9be2bff4d05c1a6
Source dataset
uspto-grants-2001_12
Patent number
US06329387B2

Reaction notes

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