Dimethylamine → 2-[(5S)-3-[6-(Dimethylamino)pyridin-3-yl]-2-oxo-5-(propan-2-yl)imidazolidin-1-yl]-N-[3-(trifluoromethyl)phenyl]acetamide

HRID 2401285Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2401285
Br[C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:12][C@H:11]([CH:13]([CH3:15])[CH3:14])[N:10]([CH2:16][C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)=[O:18])[C:9]2=[O:30])=[CH:4][CH:3]=1.[CH3:31][NH:32][CH3:33].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH3:31][N:32]([CH3:33])[C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:12][C@H:11]([CH:13]([CH3:15])[CH3:14])[N:10]([CH2:16][C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)=[O:18])[C:9]2=[O:30])=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 674DimethylamineHCID 634876Binap, (A+-)-HCID 23665647Potassium tert-butoxideHCID 86705191HCID 86705191, Verbindung

Produkt 1

HCID 867051922-[(5S)-3-[6-(Dimethylamino)pyridin-3-yl]-2-oxo-5-(propan-2-yl)imidazolidin-1-yl]-N-[3-(trifluoromethyl)phenyl]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 2-[(5S)-3-(6-bromopyridin-3-yl)-2-oxo-5-(propan-2-yl)imidazolidin-1-yl]-N-[3-(trifluoromethyl)phenyl]acetamide (250 mg) and dimethyl amine (2M solution in THF, 1.3 mL), Pd2(dba)3 (24 mg), BINAP (32 mg), and potassium tert-butoxide (87 mg) in toluene (5 mL) was stirred at 120° C. for 2 hr. Water was added thereto, the mixture was extracted with chloroform, and the organic layer was concentrated under reduced pressure. The residue was purified by preparative HPLC and PTLC (hexane/ethyl acetate=1:1) to afford the title compound (34 mg).

Aufarbeitung

  1. extractionthe mixture was extracted with chloroform
  2. concentrationthe organic layer was concentrated under reduced pressure
  3. customThe residue was purified by preparative HPLC and PTLC (hexane/ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-cc904d5e71694f9a8b1a854bdbd9293a
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08796272B2

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