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

HRID 1265026Notes

Reaction equation

HRID 1265026 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:5]([NH2:10])=[N:6][O:7][C:8]=1[CH3:9].[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]([NH:10][S:20]([C:13]2[C:14]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[S:11][CH:12]=2)(=[O:22])=[O:21])=[N:6][O:7][C:8]=1[CH3:9]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 180092614-Chloro-5-methyl-1,2-oxazol-3-amineHCID 18614041Thieno[2,3-b]pyridine-3-sulfonyl chloride

Product 1

HCID 18614046N-(4-chloro-5-methyl-3-isoxazolyl)thieno[2,3-b]pyridine-3-sulfonamideYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by the method of Example 1(C) using NaH (0.12 g, 4.9 mmoles), THF (6 ml), 4-chloro-5-methyl-3-aminoisoxazole (0.26 g, 2.0 mmoles) and thieno[2,3-b]pyridine-3-sulfonyl chloride (0.50 g, 2.1 mmoles), giving 0.30 g (47%) of the title compound as an orange-brown oil.

Workup

  1. customThe title compound was prepared by the method of Example 1(C)

Sources & evidence

ORD record
ord-d01ff0d847dd4aedbae26c55741040af
Source dataset
uspto-grants-2003_04
Patent number
US06545014B2

Reaction notes

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