2-Chlorobenzenesulfonyl chloride → HCID 66598227, compound

HRID 334765Notes

Reaction equation

HRID 334765 reaction equation
[F:1][CH2:2][C:3]1[N:8]=[C:7]([C:9]#[C:10][CH2:11][CH2:12][NH:13][CH3:14])[CH:6]=[CH:5][CH:4]=1.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22](Cl)(=[O:24])=[O:23]>>[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22]([N:13]([CH2:12][CH2:11][C:10]#[C:9][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:2][F:1])[N:8]=1)[CH3:14])(=[O:24])=[O:23]

Participants

3

Reactant 2

HCID 761872-Chlorobenzenesulfonyl chlorideHCID 665983664-(6-(fluoromethyl)pyridin-2-yl)-N-methylbut-3-yn-1-amine

Product 1

HCID 66598227HCID 66598227, compoundYield 31%

Procedure

The title compound was prepared in accordance with the general method of Example 199(D), from 4-(6-(fluoromethyl)pyridin-2-yl)-N-methylbut-3-yn-1-amine (70 mg, 0.36 mmol) and 2-chlorobenzene-1-sulfonyl chloride (92 mg, 0.44 mmol). The crude residue was purified over silicagel chromatography (prepacked 10 g silicagel column, Cyclohexane/AcOEt: 70/30 as eluent) to afford 41 mg of 2-chloro-N-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)-N-methylbenzenesulfonamide as a yellow oil (Yield: 31%).

Workup

  1. customThe crude residue was purified over silicagel chromatography (prepacked 10 g silicagel column, Cyclohexane/AcOEt: 70/30 as eluent)

Sources & evidence

ORD record
ord-0094844c5a414aecad149290daeb725f
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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