2,6-Dichlorobenzoyl chloride → HCID 66598318, compound

HRID 334766Notes

Reaction equation

HRID 334766 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:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:17]=1[C:18](Cl)=[O:19]>>[Cl:15][C:16]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:17]=1[C:18]([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:19]

Participants

3

Reactant 2

HCID 783922,6-Dichlorobenzoyl chlorideHCID 665983664-(6-(fluoromethyl)pyridin-2-yl)-N-methylbut-3-yn-1-amine

Product 1

HCID 66598318HCID 66598318, compoundYield 5.4%

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 (180 mg, 0.93 mmol) and 2,6-dichlorobenzoyl chloride (255 mg, 1.22 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 18.5 mg of 2,6-dichloro-N-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)-N-methylbenzamide as a yellow oil (Yield: 5%).

Workup

  1. customThe crude residue was purified over silicagel chromatography (prepacked 10 g silicagel column, DCM/MeOH: from 100/0 to 98/2 as eluent)

Sources & evidence

ORD record
ord-18d271fc6363437db9f132ed2d265eba
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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