Triethylamine → HCID 66750848, compound

HRID 534999Notes

Reaction equation

HRID 534999 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)([CH3:6])([CH3:5])[CH3:4].[CH2:20]([O:22][C:23](=[O:28])[CH2:24][C:25](O)=[O:26])[CH3:21].C(N(CC)CC)C.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C([O-])(O)=O.[Na+]>CN(C)C=O>[C:3]([C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[N:14]1[CH2:19][CH2:18][N:17]([C:25](=[O:26])[CH2:24][C:23]([O:22][CH2:20][CH3:21])=[O:28])[CH2:16][CH2:15]1)([CH3:6])([CH3:4])[CH3:5]

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 70615Monoethyl malonateHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 66750915HCID 66750915, compound

Product 1

HCID 66750848HCID 66750848, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(2-tert-butyl-4-chlorophenyl)piperazine dihydrochloride (Reference Example 20, 0.40 g, 1.23 mmol), 3-ethoxy-3-oxopropanoic acid (0.19 g, 1.47 mmol), triethylamine (514 μL, 3.69 mmol), EDCI (0.23 g, 1.47 mmol) and HOBt (0.23 g, 1.47 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 16 h. The reaction mixture was added to saturated NaHCO3 solution and extracted with ethyl acetate. The extract was washed with saturated NaHCO3 solution and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate 80:20 to 20:80) to give the title compound (0.39 g, 87%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated NaHCO3 solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate 80:20 to 20:80)

Sources & evidence

ORD record
ord-d990c72a5f8a4a1b908fb6f49649493b
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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