Triethylamine → HCID 18518631, compound

HRID 1369067

Reaction equation

HRID 1369067 reaction equation
[C:1]([OH:7])(=O)[CH2:2][CH2:3][C:4]#[CH:5].Cl.[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>CN(C=O)C.O>[O:12]1[CH2:13][CH2:14][N:9]([C:1]([C:2]#[C:3][CH2:4][CH3:5])=[O:7])[CH2:10][CH2:11]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 224644-Pentynoic acidHCID 757711-HydroxybenzotriazoleHCID 197884Morpholine, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 18518631HCID 18518631, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-pentynoic acid (210 mg, 2.14 mmol), morpholine hydrochloride (265 mg, 2.14 mmol), 1-hydroxybenzotriazol (338 mg, 2.50 mmol), WSC HCl (484 mg, 2.52 mmol), and triethylamine (0.37 ml, 2.65 mmol) in DMF (7 mL) was stirred for 1 h at room temperature. Water was added. The mixture was extracted with ethyl acetate-toluene, and the extracts were washed with water, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography with 1:1 to 1:5 hexane/ethyl acetate to give the title compound (325 mg, 91%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate-toluene
  2. washthe extracts were washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography with 1:1 to 1:5 hexane/ethyl acetate

Sources & evidence

ORD record
ord-e463d08e0f1d47378e7dfcdfe5f8ba71
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Linked notes

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