N,N-Dimethylpiperidin-4-amine → HCID 66977664, Verbindung

HRID 77106

Reaktionsgleichung

Reaktionsgleichung von HRID 77106
Cl.[CH3:2][N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[C:12]1[CH:13]=[C:14]([N:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([C:24](O)=[O:25])[CH2:19]2)[CH:15]=[CH:16][CH:17]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:51][N:52]([CH:54]1[CH2:59][CH2:58][NH:57][CH2:56][CH2:55]1)[CH3:53]>>[NH3:3].[CH3:51][N:52]([CH3:53])[CH:54]1[CH2:59][CH2:58][N:57]([C:24]([C@@H:20]2[CH2:21][CH2:22][CH2:23][N:18]([C:14]3[CH:15]=[CH:16][CH:17]=[C:12]([C:4]4[N:3]([CH3:2])[C:7]5[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=5[N:5]=4)[CH:13]=3)[CH2:19]2)=[O:25])[CH2:56][CH2:55]1

Komponenten

5

Edukt 3

HCID 417391N,N-Dimethylpiperidin-4-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66977536(R)-1-[3-(1-methyl-1H-benzoimidazol-2-yl)-phenyl]-piperidine-3-carboxylic acid hydrochloride

Produkt 2

HCID 222AmmoniaHCID 66977664HCID 66977664, VerbindungAusbeute 74,8 %

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

Method N—Step a To a mixture of (R)-1-[3-(1-methyl-1H-benzoimidazol-2-yl)-phenyl]-piperidine-3-carboxylic acid hydrochloride (obtained as described in general method 1, step d) (0.01 g, 0.30 mmol) (obtained as described in method A, step d) in dcm (2.5 mL), HATU (0.12 g, 0.33 mmol), TEA (0.09 mL, 0.63 mmol) and 4-(N,N-dimethylamino)piperidine (0.04 g, 0.35 mmol) were added. The reaction mixture was heated at 35° C. overnight, cooled to room temperature, washed with ammonium chloride solution (3 mL), filtered through a phase separator and organic solvent was removed. The crude was then purified by SCX column (eluent: first dcm:MeOH/1:1 then NH3 in MeOH (2N)) and flash chromatography (eluent: gradient from EtOAc:NH3 in MeOH (2N)/10:0 to 9:1) to obtain 0.05 g of the title compound (37%).

Aufarbeitung

  1. additionwere added
  2. temperaturecooled to room temperature
  3. washwashed with ammonium chloride solution (3 mL)
  4. filtrationfiltered through a phase separator and organic solvent
  5. customwas removed
  6. customThe crude was then purified by SCX column (eluent

Quellen und Nachweise

ORD-Eintrag
ord-59a2a3a174474170904c8e35fd4bc755
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835648B2

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