Triethylamine → HCID 67165955, Verbindung

HRID 877373Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 877373
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[Cl-].[C:15]([CH:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH3+:18])#[N:16].Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.C(N(CC)CC)C>O.C(Cl)Cl>[C:15]([CH:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH:18][C:11](=[O:13])[CH2:10][C:7]1[CH:6]=[CH:5][C:4]([CH:1]([CH3:2])[CH3:3])=[CH:9][CH:8]=1)#[N:16]

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 408372-Amino-2-phenylacetonitrile hydrochlorideHCID 782304-Isopropylphenylacetic acidHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 67165955HCID 67165955, VerbindungAusbeute 54,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a 100 ml round bottom flask equipped with a magnetic stir bar were added 4-isopropylphenylacetic acid (1.786 g, 10.02 mmol), cyano(phenyl)-methanaminium chloride (1.690 g, 10.02 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.921 g, 10.02 mmol), 1-hydroxy-7-azabenzotriazole (1.364 g, 10.02 mmol) and triethylamine (3.042 ml, 30.06 mmol) into 30.0 ml of CH2Cl2. The resulting solution was stirred at room temperature for 16 hours. The reaction mixture was diluted with water and the two layers were separated. The aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuum. Purification by preparative HPLC (20-90% CH3CN/H2O over 30 min, 0.05% added TFA, C18 column) to afford 1.6 g (54%) of the title compound. 1H NMR (CDCl3, 400 MHz) δ 7.382 (m, 5H), 7.206 (m, 4H), 6.156 (d, J=8.6 Hz, 1H), 5.997 (br d, J=8.2 Hz, 1H), 3.632 (s, 2H), 2.895 (sept, J=7.0 Hz, 1H), 1.238 (d, J=7.0 Hz, 6H). ES-MS [M+1]+: 293.2.

Aufarbeitung

  1. customTo a 100 ml round bottom flask equipped with a magnetic stir bar
  2. customthe two layers were separated
  3. extractionThe aqueous layer was extracted with CH2Cl2
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuum
  8. customPurification
  9. additionby preparative HPLC (20-90% CH3CN/H2O over 30 min, 0.05% added TFA, C18 column)

Quellen und Nachweise

ORD-Eintrag
ord-5466ea500c90474dae7bb2bb9e1f4a32
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987310B2

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