2-(Trifluoromethyl)benzoyl chloride → HCID 66598238, compound

HRID 1189281Notes

Reaction equation

HRID 1189281 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.[F:13][C:14]([F:25])([F:24])[C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=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]=[CH:23][C:15]=1[C:14]([F:13])([F:24])[F:25]

Participants

3

Reactant 2

HCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 66598286N-methyl-4-(pyridin-2-yl)but-3-yn-1-amine

Product 1

HCID 66598238HCID 66598238, compoundYield 61.2%

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 2-(trifluoromethyl)benzoyl chloride (80 mg, 0.41 mmol). The crude residue was purified over silicagel chromatography (prepacked 10 g silicagel column, DCM/MeOH: from 100/0 to 97/3 as eluent) to afford 63 mg of N-methyl-N-(4-(pyridin-2-yl)but-3-ynyl)-2-(trifluoromethyl)benzamide as a brown oil (Yield: 61%).

Workup

  1. customThe crude residue was purified over silicagel chromatography (prepacked 10 g silicagel column, DCM/MeOH: from 100/0 to 97/3 as eluent)

Sources & evidence

ORD record
ord-2ce59f0fb36e4644980937a1aabcd61c
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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