Benzoyl chloride, 3-bromo- → 3-Bromo-N-(4-(2-methoxyethoxy)-3-(2-methyl-2H-pyrazol-3-yl)phenyl)benzamide

HRID 1507076Notes

Reaction equation

HRID 1507076 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].C(N(CC)C(C)C)(C)C.[CH3:20][O:21][CH2:22][CH2:23][O:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][C:26]=1[C:32]1[N:33]([CH3:37])[N:34]=[CH:35][CH:36]=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:29][C:28]1[CH:30]=[CH:31][C:25]([O:24][CH2:23][CH2:22][O:21][CH3:20])=[C:26]([C:32]2[N:33]([CH3:37])[N:34]=[CH:35][CH:36]=2)[CH:27]=1)=[O:6]

Participants

5

Reactant 3

HCID 74377Benzoyl chloride, 3-bromo-HCID 81531DiisopropylethylamineHCID 577866324-(2-Methoxyethoxy)-3-(2-methyl-2H-pyrazol-3-yl)aniline

Product 1

HCID 248884953-Bromo-N-(4-(2-methoxyethoxy)-3-(2-methyl-2H-pyrazol-3-yl)phenyl)benzamideYield 99.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-bromobenzoyl chloride (0.06 mmol), N,N-diisopropylethylamine (14 μL, 0.08 mmol), and 4-(2-methoxyethoxy)-3-(2-methyl-2H-pyrazol-3-yl)aniline (0.05 mmol) in 0.28 mL DMF was agitated on a mechanical shaker for 2 hours. The product was isolated by RP-HPLC and lyophilized to give the title compound (21.4 mg, 96%). LCMS m/z (%)=432.3 (M+H, 81Br 100.0), 430.3 (M+H, 79Br 87.6).

Workup

  1. customThe product was isolated by RP-HPLC

Sources & evidence

ORD record
ord-737b27009b4845ab9361ef6504909f5f
Source dataset
uspto-grants-2015_12
Patent number
US09221755B2

Reaction notes

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