Triethylamine → HCID 23157523, compound

HRID 508059Notes

Reaction equation

HRID 508059 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][C:22]3[CH:32]=[CH:31][C:25]([O:26][CH2:27][C:28]([OH:30])=O)=[CH:24][CH:23]=3)[CH:15]=2)=[C:9]([CH3:33])[CH:8]=1)[CH3:2].Cl.[CH3:35][NH:36][O:37][CH3:38].C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH3:33])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][C:22]3[CH:23]=[CH:24][C:25]([O:26][CH2:27][C:28]([N:36]([O:37][CH3:38])[CH3:35])=[O:30])=[CH:31][CH:32]=3)[CH:15]=2)=[C:11]([CH3:13])[CH:12]=1)[CH3:2]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23157653HCID 23157653, compound

Product 1

HCID 23157523HCID 23157523, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [4-({[4′-(2-ethoxyethoxy)-2′,6′-dimethylbiphenyl-3-yl]methyl}amino)phenoxy]acetic acid (0.22 g, 0.49 mmol), N,O-dimethylhydroxylamine hydrochloride (72 mg, 0.74 mmol), triethylamine (0.12 mL, 0.86 mmol) and 1-hydroxybenzotriazole (98 mg, 0.64 mmol) in N,N-dimethylformamide (15 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (122 mg, 0.64 mmol) under ice-cooling, and the mixture was stirred at room temperature for 18 hr. The reaction solution was diluted with ethyl acetate, washed successively with aqueous citric acid solution, water and aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5-2:1) to give the title compound (160 mg, yield 66%) as a colorless oil.

Workup

  1. temperaturecooling
  2. washwashed successively with aqueous citric acid solution, water and aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5-2:1)

Sources & evidence

ORD record
ord-f5c5ef4185e5444d84adacd10c3421e2
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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