Diisopropylethylamine → HCID 67509427, Verbindung

HRID 623574

Reaktionsgleichung

Reaktionsgleichung von HRID 623574
Cl.[F:2][C:3]([F:16])([F:15])[CH2:4][O:5][C:6]1[N:11]=[CH:10][C:9]([CH:12]([NH2:14])[CH3:13])=[CH:8][CH:7]=1.[NH2:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][N:26]=1)[C:21](O)=[O:22].C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O>[NH2:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][N:26]=1)[C:21]([NH:14][CH:12]([C:9]1[CH:10]=[N:11][C:6]([O:5][CH2:4][C:3]([F:2])([F:15])[F:16])=[CH:7][CH:8]=1)[CH3:13])=[O:22]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 2783962-Aminopyridine-4-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 675094131-[6-(2,2,2-Trifluoroethoxy)-pyridin-3-yl]-ethylamine hydrochloride

Produkt 1

HCID 67509427HCID 67509427, VerbindungAusbeute 63,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of (−)-1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanamine hydrochloride (300 mg, 1.17 mmol, Amine-1, single enantiomer), 2-aminoisonicotinic acid (161 mg, 1.17 mmol), and N,N-diisopropylethylamine (0.82 mL, 4.68 mmol) in N,N-dimethylformamide (12 mL) is added HBTU (665 mg, 1.75 mmol) at room temperature. After stirring at room temperature for 1 hour, the mixture is poured onto water (20 mL), and the mixture is extracted with ethyl acetate (20 mL). The organic layer is dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel eluting with dichloromethane/methanol (10:1) to give 252 mg (63% yield) of the title compound as a slight brown solid.

Aufarbeitung

  1. additionthe mixture is poured onto water (20 mL)
  2. extractionthe mixture is extracted with ethyl acetate (20 mL)
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by column chromatography on silica gel eluting with dichloromethane/methanol (10:1)

Quellen und Nachweise

ORD-Eintrag
ord-073f52c1a25045988e51a1d45eb0357c
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09302991B2

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