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

HRID 1265011Notes

Reaction equation

HRID 1265011 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:5]([NH2:10])=[N:6][O:7][C:8]=1[CH3:9].[CH2:11]([C:13]1[S:21][C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[C:14]=1[S:22](Cl)(=[O:24])=[O:23])[CH3:12]>C1COCC1>[Cl:3][C:4]1[C:5]([NH:10][S:22]([C:14]2[C:15]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[S:21][C:13]=2[CH2:11][CH3:12])(=[O:24])=[O:23])=[N:6][O:7][C:8]=1[CH3:9]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 120449152-Ethylthieno[2,3-b]pyridine-3-sulfonyl chlorideHCID 180092614-Chloro-5-methyl-1,2-oxazol-3-amine

Product 1

HCID 12044905N-(4-chloro-5-methyl-3-isoxazolyl)-2-ethylthieno[2,3-b]pyridine-3-sulfonamideYield 35.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(4-chloro-5-methyl-3-isoxazolyl)-2-ethylthieno[2,3-b]pyridine-3-sulfonamide was prepared according to Example 1 (C), using NaH (44 mg, 1.9 mmoles), THF (5 ml), 4-chloro-5-methyl-3-aminoisoxazole (82 mg, 0.62 mmoles) and 2-ethylthieno[2,3-b]pyridine-3-sulfonyl chloride (0.19 g, 0.71 mmoles). Flash chromatography (50% EtOAc/hexanes) followed by recrystallization from EtOAc/hexanes provided 78 mg (35%) of the title compound as a light yellow solid, m.p. 172-174° C.

Workup

  1. customN-(4-chloro-5-methyl-3-isoxazolyl)-2-ethylthieno[2,3-b]pyridine-3-sulfonamide was prepared
  2. customFlash chromatography (50% EtOAc/hexanes) followed by recrystallization from EtOAc/hexanes

Sources & evidence

ORD record
ord-bfc7d695b4204dc49ce6d2164225fa06
Source dataset
uspto-grants-2003_04
Patent number
US06545014B2

Reaction notes

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