3-Methylbenzoyl chloride → N,3-dimethyl-N-(4-(pyridin-2-yl)but-3-ynyl)benzamide

HRID 1189297Notes

Reaction equation

HRID 1189297 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[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17](Cl)=[O:18]>>[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)[C:17](=[O:18])[C:16]1[CH:20]=[CH:21][CH:22]=[C:14]([CH3:13])[CH:15]=1

Participants

3

Reactant 2

HCID 743753-Methylbenzoyl chlorideHCID 66598286N-methyl-4-(pyridin-2-yl)but-3-yn-1-amine

Product 1

HCID 66598288N,3-dimethyl-N-(4-(pyridin-2-yl)but-3-ynyl)benzamideYield 29%

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-methylbenzoyl chloride (58 mg, 0.37 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 25 mg of N,3-dimethyl-N-(4-(pyridin-2-yl)but-3-ynyl)benzamide as a yellow pale oil (Yield: 29%).

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-96bac58ca4904d74b17a5fbf0750cb85
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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