O-ethylhydroxylamine hydrochloride → N-Ethoxy-3-[(4-iodo-2-methylphenyl)amino]isonicotinamide

HRID 78764Notes

Reaction equation

HRID 78764 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:17]=[N:16][CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=O)=[C:4]([CH3:18])[CH:3]=1.CCN(C(C)C)C(C)C.Cl.[CH2:29]([O:31][NH2:32])[CH3:30]>CN(C=O)C>[CH2:29]([O:31][NH:32][C:11](=[O:13])[C:10]1[CH:14]=[CH:15][N:16]=[CH:17][C:9]=1[NH:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][C:4]=1[CH3:18])[CH3:30]

Participants

5

Reactant 3

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 576496173-[(2-Methyl-4-iodophenyl)amino]isonicotinic acid

Product 1

HCID 57649631N-Ethoxy-3-[(4-iodo-2-methylphenyl)amino]isonicotinamideYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[(4-iodo-2-methylphenyl)amino]isonicotinic acid 2c (60 mg, 0.17 mmol) was dissolved in 6 ml dry DMF followed by the addition of DIPEA (0.20 mmol, 37 μl), ByBOP (0.20 mmol, 107 mg) and O-ethylhydroxylamine hydrochloride (0.34 mmol, 34 mg). The mixture was stirred for 4 h and the volatiles were removed in vacuo. The crude material was purified by preparative reversed phase HPLC to give 36 mg (91 μmol; 53% yield) of pure desired product.

Workup

  1. customthe volatiles were removed in vacuo
  2. customThe crude material was purified by preparative reversed phase HPLC

Sources & evidence

ORD record
ord-07434e418da045c8b635ed127911d12c
Source dataset
uspto-grants-2014_09
Patent number
US08841459B2

Reaction notes

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