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Triethylamine → 3,4-Dichloro-N-[1-(2-chloropyrimidin-4-yl)piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide

HRID 2234041
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2234041
Cl.[Cl:2][C:3]1[C:7]([Cl:8])=[C:6]([CH3:9])[NH:5][C:4]=1[C:10]([NH:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:11].[Cl:19][C:20]1[N:25]=[C:24](Cl)[CH:23]=[CH:22][N:21]=1.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.O>[Cl:2][C:3]1[C:7]([Cl:8])=[C:6]([CH3:9])[NH:5][C:4]=1[C:10]([NH:12][CH:13]1[CH2:18][CH2:17][N:16]([C:22]2[CH:23]=[CH:24][N:25]=[C:20]([Cl:19])[N:21]=2)[CH2:15][CH2:14]1)=[O:11]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 775312,4-DichloropyrimidineHCID 68579996HCID 68579996, Verbindung2×

Produkt 1

HCID 866083433,4-Dichloro-N-[1-(2-chloropyrimidin-4-yl)piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamideAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel
HCID 6228DimethylformamideLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

3,4-Dichloro-5-methyl-N-piperidin-4-yl-1H-pyrrole-2-carboxamide hydrochloride (Intermediate 1, 650 mg, 2.08 mmol), 2,4-dichloropyrimidine (309.7 mg, 2.08 mmol), and Et3N (0.6 ml, 4.16 mmol) were combined in DMF (12 ml) and heated at 90° C. under nitrogen for 1.5 h. Upon cooling to room temperature, the reaction was diluted with EtOAc and water. The phases were separated, and the aqueous portion was extracted twice with EtOAc. The combined organic portions were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give a light brown solid. The crude material was triturated with cold MeOH and filtered to give 458 mg (1.18 mmol, 57%) of the title product.

Aufarbeitung

  1. temperatureUpon cooling to room temperature
  2. customThe phases were separated
  3. extractionthe aqueous portion was extracted twice with EtOAc
  4. washThe combined organic portions were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a light brown solid
  9. customThe crude material was triturated with cold MeOH
  10. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-4efd95c46d8143f1b7a1a4958292d895
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07709503B2

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