Triethylamine → HCID 66750860, Verbindung

HRID 534994

Reaktionsgleichung

Reaktionsgleichung von HRID 534994
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:21])[C:18](O)=[O:19])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:23][CH2:24][CH2:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=1.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:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][N:14]([C:17](=[O:21])[C:18]([NH:23][CH2:24][CH2:25][C:26]2[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=2)=[O:19])[CH2:15][CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

8

Edukt 6

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 13078671Methyl 4-(2-aminoethyl)benzoate hydrochlorideHCID 66750854HCID 66750854, Verbindung

Produkt 1

HCID 66750860HCID 66750860, VerbindungAusbeute 71,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoacetic acid (Example 44, 1.0 g, 3.44 mmol), methyl 4-(2-aminoethyl)benzoate hydrochloride (0.83 g, 4.13 mmol), triethylamine (0.72 mL, 5.16 mmol), EDCI (0.64 g, 4.13 mmol) and HOBt (0.63 g, 4.13 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 16 h. The reaction mixture was poured into 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 34:66) to give the title compound (1.11 g, 71%) as a white amorphous.

Aufarbeitung

  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 34:66)

Quellen und Nachweise

ORD-Eintrag
ord-375f6e52ea0e48eca00b0610d81ad806
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853215B2

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