Triethylamine → HCID 23136340, compound

HRID 1678605Notes

Reaction equation

HRID 1678605 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][CH2:6][C:7]1[CH:25]=[CH:24][C:10]([O:11][CH2:12][C:13]2[CH:14]=[C:15]([CH:21]=[CH:22][CH:23]=2)[O:16][CH2:17][C:18](O)=[O:19])=[C:9]([F:26])[CH:8]=1)[CH3:2].Cl.CN.[CH2:31]([N:33](CC)CC)C.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C=O)C.O>[F:26][C:9]1[CH:8]=[C:7]([CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:27])[CH:25]=[CH:24][C:10]=1[O:11][CH2:12][C:13]1[CH:23]=[CH:22][CH:21]=[C:15]([O:16][CH2:17][C:18]([NH:33][CH3:31])=[O:19])[CH:14]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6364545Methylamine hydrochlorideHCID 23136295HCID 23136295, compound

Product 1

HCID 23136340HCID 23136340, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of (3-{[4-(3-ethoxy-3-oxopropyl)-2-fluorophenoxy]methyl}phenoxy)acetic acid (0.34 g, 0.90 mmol), methylamine hydrochloride (0.073 g, 1.08 mmol), triethylamine (0.22 g, 2.16 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.21 g, 1.08 mmol) and 1-hydroxybenzotriazole (0.15 g, 1.08 mmol) in DMF (7 mL) was stirred at room temperature for 18 hours. Then, water was added to the reaction mixture and extracted with ethyl acetate. The organic layer was washed successively with saturated brine and water, and concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=2:8) to give the title compound (0.34 g, yield 97%) as an oily matter.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed successively with saturated brine and water
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=2:8)

Sources & evidence

ORD record
ord-1225a844155f413c8a7bf9236e0b6a19
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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