3,5-Dimethylisoxazole-4-sulfonyl chloride → HCID 66598388, compound

HRID 422485Notes

Reaction equation

HRID 422485 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]#[C:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.[CH3:13][C:14]1[C:18]([S:19](Cl)(=[O:21])=[O:20])=[C:17]([CH3:23])[O:16][N:15]=1>>[CH3:1][N:2]([CH2:3][CH2:4][C:5]#[C:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)[S:19]([C:18]1[C:14]([CH3:13])=[N:15][O:16][C:17]=1[CH3:23])(=[O:21])=[O:20]

Participants

3

Reactant 2

HCID 27363193,5-Dimethylisoxazole-4-sulfonyl chlorideHCID 66598286N-methyl-4-(pyridin-2-yl)but-3-yn-1-amine

Product 1

HCID 66598388HCID 66598388, compoundYield 17.2%

Procedure

The title compound was prepared in accordance with the general method of Example 199(D), from N-methyl-4-(pyridin-2-yl)but-3-yn-1-amine (50 mg, 0.31 mmol) and 3,5-dimethylisoxazole-4-sulfonyl chloride (79 mg, 0.41 mmol). The crude residue was purified over silicagel chromatography prepacked 10 g silicagel column, DCM/MeOH: from 100/0 to 98/2 as eluent) to afford 17 mg of N,3,5-trimethyl-N-(4-(pyridin-2-yl)but-3-ynyl)isoxazole-4-sulfonamide as a brown oil (Yield: 17%).

Workup

  1. customThe crude residue was purified over silicagel chromatography

Sources & evidence

ORD record
ord-42c51e7650ed41d68ffab9561b41ab61
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

Loading…