N,1-dimethylpyrrolidin-3-amine → HCID 178480456, Verbindung

HRID 77102

Reaktionsgleichung

Reaktionsgleichung von HRID 77102
Cl.[Cl:2][C:3]1[CH:27]=[CH:26][C:6]2[NH:7][C:8]([C:10]3[CH:11]=[C:12]([N:17]4[CH2:22][CH2:21][CH:20]([C:23]([OH:25])=O)[CH2:19][CH2:18]4)[CH:13]=[CH:14][C:15]=3[F:16])=[N:9][C:5]=2[CH:4]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:52][NH:53][CH:54]1[CH2:58][N:57]([CH3:59])[CH2:56][CH2:55]1>>[CH3:52][N:53]([CH:54]1[CH2:55][CH2:56][N:57]([CH3:59])[CH2:58]1)[C:23]([CH:20]1[CH2:21][CH2:22][N:17]([C:12]2[CH:13]=[CH:14][C:15]([F:16])=[C:10]([C:8]3[NH:7][C:6]4[CH:26]=[CH:27][C:3]([Cl:2])=[CH:4][C:5]=4[N:9]=3)[CH:11]=2)[CH2:18][CH2:19]1)=[O:25]

Komponenten

4

Edukt 3

HCID 2758520N,1-dimethylpyrrolidin-3-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178479749HCID 178479749, Verbindung

Produkt 1

HCID 178480456HCID 178480456, VerbindungAusbeute 30 %

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

Method J—Step a To a mixture of 1-[3-(5-Chloro-1H-benzoimidazol-2-yl)-4-fluoro-phenyl]-piperidine-4-carboxylic acid hydrochloride (obtained as described in general method 10, step b) (0.01 g, 0.25 mmol) in dcm (2 mL), HATU (0.10 g, 0.26 mmol), TEA (0.07 mL, 0.55 mmol) and N,N′-dimethyl-3-aminopyrrolidine (0.04 g, 0.31 mmol) were added. The reaction mixture was heated at 35° C. overnight, cooled to room temperature and washed with ammonium chloride solution (2 mL), saturated Na2CO3 solution (2 mL) and water (2 mL). The organic layer was then filtrated on an NH2 cartridge and further purified by flash chromatography (eluent: EtOAc:NH3 2N in MeOH/9:1) to obtain 0.03 g of the title compound (30%).

Aufarbeitung

  1. additionwere added
  2. temperaturecooled to room temperature
  3. washwashed with ammonium chloride solution (2 mL), saturated Na2CO3 solution (2 mL) and water (2 mL)
  4. filtrationThe organic layer was then filtrated on an NH2 cartridge
  5. customfurther purified by flash chromatography (eluent: EtOAc:NH3 2N in MeOH/9:1)

Quellen und Nachweise

ORD-Eintrag
ord-5a847595c8984844a698703d86c9781a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835648B2

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