Triethylamine → 3-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]-N-methoxy-N-methylpropionamide

HRID 452709Notes

Reaction equation

HRID 452709 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:14][C:13]([CH2:15][CH2:16][C:17]([OH:19])=O)=[N:12][N:11]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1.Cl.[CH3:21][NH:22][O:23][CH3:24].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:14][C:13]([CH2:15][CH2:16][C:17]([N:22]([O:23][CH3:24])[CH3:21])=[O:19])=[N:12][N:11]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 621995883-[5-(2,3-Dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]propionic acid

Product 1

HCID 866400353-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]-N-methoxy-N-methylpropionamideYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 3-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]propionic acid (3.00 g, 11.53 mmol), N,O-dimethylhydroxyamine hydrochloride (2.25 g, 23.06 mmol), triethylamine (4.0 mL, 28.83 mmol), 3-(3-dimethylaminopropyl)-1-ethylcarbodiimide hydrochloride (3.32 g, 17.30 mmol) and 1-hydroxybenzotriazole (2.34 g, 17.30 mmol) in N,N-dimethylformamide (50 mL) was stirred at room temperature for 16 hr. The reaction mixture was diluted with ethyl acetate, washed with water, aqueous sodium hydroxide solution, hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from hexane/ethyl acetate to give the title compound (2.75 g, yield 79%) as colorless crystals.

Workup

  1. washwashed with water, aqueous sodium hydroxide solution, hydrochloric acid and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-18b0bab2401642009b276a5209823aa7
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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