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Triethylamine → HCID 10906711, Verbindung

HRID 1432919
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1432919
C(N(CC)CC)C.[CH2:8]([O:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]#[CH:26])[C:20](=[O:27])[CH2:19]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:28]([O:32][C:33](=[O:42])[NH:34][C:35]1[CH:40]=[CH:39][N:38]=[CH:37][C:36]=1I)([CH3:31])([CH3:30])[CH3:29].C1CCN2C(=NCCC2)CC1>CN(C=O)C.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:28]([O:32][C:33]([N:34]1[C:35]2[CH:40]=[CH:39][N:38]=[CH:37][C:36]=2[CH:26]=[C:25]1[CH2:24][N:21]1[CH2:22][CH2:23][N:18]([C:16]([O:15][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:17])[CH2:19][C:20]1=[O:27])=[O:42])([CH3:31])([CH3:29])[CH3:30]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 8471TriethylamineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10891001Benzyl 3-oxo-4-(prop-2-yn-1-yl)piperazine-1-carboxylateHCID 10903275(3-Iodo-pyridin-4-yl)-carbamic acid tert-butyl ester

Produkt 1

HCID 10906711HCID 10906711, VerbindungAusbeute 76,7 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Pd(PPh3)2Cl2 (0.29 g, 0.41 mmol), CuI (0.05 g, 0.25 mmol) and triethylamine (4.6 mL, 3.29 mmol) is added to a solution of 3-oxo-4-prop-2-ynylpiperazine-1-carboxylic acid benzyl ester (2.24 g, 8.23 mmol) and (3-iodopyridin-4-yl)-carbamic acid tert-butyl ester (2.63 g, 8.23 mmol) in DMF (30 mL) at room temperature. The mixture is heated to 100° C. and stirred for 1.5 hours. The reaction mixture is then cooled to 50° C. and DBU (2.5 mL, 16.5 mmol) is added. After 30 minutes the solution is cooled to room temperature, diluted with ethyl acetate and washed with saturated ammonium chloride, water and brine. The organic layer is dried over MgSO4, filtered and concentrated in vacuo. The resulting solid is purified by column chromatography eluting with a gradient of 2% MeOH/CH2Cl2to 5% MeOH/CH2Cl2to give the product (2.93 g, 6.31 mmol) as a white solid. 1H NMR (CDCl3, 300 MHz) δ8.75 (s, 1H), 8.4 (d, 1H), 7.85 (d, 1H), 7.35 (m, 5H), 6.38 (s, 1H), 5.2 (s, 2H), 5.00 (s, 2H), 4.29 (s, 2H), 3.85 (m, 2H), 3.52 (m, 2H), 1.7 (s, 9H). Ion spray MS, [M+H]+=465.

Aufarbeitung

  1. temperatureThe reaction mixture is then cooled to 50° C.
  2. temperatureAfter 30 minutes the solution is cooled to room temperature
  3. washwashed with saturated ammonium chloride, water and brine
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting solid is purified by column chromatography
  8. washeluting with a gradient of 2% MeOH/CH2Cl2to 5% MeOH/

Quellen und Nachweise

ORD-Eintrag
ord-14df01b481304d4d9cba82da8576722d
Quelldatensatz
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07612075B2

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