4-Methylbenzoyl Chloride → HCID 66598120, compound

HRID 1189296Notes

Reaction equation

HRID 1189296 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:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH: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)[C:18](=[O:19])[C:17]1[CH:21]=[CH:22][C:14]([CH3:13])=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 134054-Methylbenzoyl ChlorideHCID 66598286N-methyl-4-(pyridin-2-yl)but-3-yn-1-amine

Product 1

HCID 66598120HCID 66598120, compoundYield 36%

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 4-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 31 mg of N,4-dimethyl-N-(4-(pyridin-2-yl)but-3-ynyl)benzamide as a brown oil (Yield: 36%).

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-fef4af90ab734306a7aa3f6724ce3650
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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