Ammonium Chloride → 2-[2-[2-(5-Cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetamide

HRID 733364Notes

Reaction equation

HRID 733364 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:29][CH3:30])=[C:7]([S:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:25]=[CH:24][C:23]([CH:26]([CH3:28])[CH3:27])=[CH:22][C:16]=2[O:17][CH2:18][C:19](O)=[O:20])(=[O:11])=[O:10])[CH:8]=1)#[N:2].[Cl-].[NH4+].O.O[N:35]1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.CN(C)CCCN=C=NCC>O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:29][CH3:30])=[C:7]([S:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:25]=[CH:24][C:23]([CH:26]([CH3:27])[CH3:28])=[CH:22][C:16]=2[O:17][CH2:18][C:19]([NH2:35])=[O:20])(=[O:11])=[O:10])[CH:8]=1)#[N:2]

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 18456942[2-[2-(5-Cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetic acid

Product 1

HCID 184569292-[2-[2-(5-Cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetamideYield 89.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.169 g of [2-[2-(5-cyano-2-methoxybenzene-sulfonylamino)ethyl]-5-isopropylphenoxy]acetic acid, 41.8 mg of ammonium chloride, 79.2 mg of 1-hydroxybenzotriazole monohydrate, 0.272 mL of N,N-diisopropylethylamine and 0.112 g of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride was stirred at room temperature for 27 hours. The reaction mixture was diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by column chromatography on aminopropylated silica gel (eluent: dichloromethane-ethyl acetate) to give 151.4 mg of 2-[2-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]acetamide.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe obtained residue was purified by column chromatography on aminopropylated silica gel (eluent: dichloromethane-ethyl acetate)

Sources & evidence

ORD record
ord-944deda2aba7444b87648c1853d7cb87
Source dataset
uspto-grants-2009_09
Patent number
US07589126B2

Reaction notes

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