Ammonium Hydroxide → 1-(4-(3,5-Dimethyl-2,4'-bipyridin-2'-yl)piperazin-1-yl)-3-(methylsulfonyl)propan-1-one

HRID 2172861Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2172861
Cl[C:2]1[C:3]([C:22]2[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][N:23]=2)=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:21])[CH2:15][CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[NH4+].[OH-]>[Pd].CO.O>[CH3:28][C:27]1[C:22]([C:3]2[CH:2]=[CH:7][N:6]=[C:5]([N:8]3[CH2:9][CH2:10][N:11]([C:14](=[O:21])[CH2:15][CH2:16][S:17]([CH3:20])(=[O:18])=[O:19])[CH2:12][CH2:13]3)[CH:4]=2)=[N:23][CH:24]=[C:25]([CH3:29])[CH:26]=1

Komponenten

5

Edukt 2

HCID 14923Ammonium HydroxideHCID 569562401-(4-(5'-Chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)piperazin-1-yl)-3-(methylsulfonyl)propan-1-one

Produkt 1

HCID 569675951-(4-(3,5-Dimethyl-2,4'-bipyridin-2'-yl)piperazin-1-yl)-3-(methylsulfonyl)propan-1-oneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 22242641Methanol--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To 1-[4-(5′-chloro-3,5-dimethyl-2,4′-bipyridin-2′-yl)piperazin-1-yl]-3-(methylsulfonyl)propan-1-one (44 mg, 0.10 mmol) was added MeOH/Water 6:1 (5 mL, 0.02M), then 10% Pd/C (25 μL=20 w/w % relative to substrate) followed by NH4OH (1.0 mL, 5 eq, 0.5M solution in MeOH). The reaction of mixture was stirred at ambient temperature at 25° C. under balloon H2 for 12 hrs. After filtering off catalyst through celite, the concentrated crude product was diluted with EtOAc (25 mL), washed with water (10 mL), then brine (10 mL), dried over MgSO4, filtered. The solution was concentrated in vacuo. The residue was purified by chromatography on silica gel (EtOAc/heptane=1:3) to give the title compound (36 mg, 90%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.36 (s, 1 H) 8.24-8.29 (m, 1 H) 7.42 (s, 1 H) 6.79-6.84 (m, 2 H) 3.75-3.81 (m, 4 H) 3.58-3.66 (m, 4 H) 3.47 (t, J=7.33 Hz, 2 H) 3.00 (s, 3H) 2.93-2.99 (m, 2 H) 2.37 (s, 3 H) 2.33 (s, 3 H); m/z for C20H26N4O3S 403.1 (M+H)+.

Aufarbeitung

  1. customThe reaction of mixture
  2. filtrationAfter filtering off catalyst through celite
  3. concentrationthe concentrated crude product
  4. additionwas diluted with EtOAc (25 mL)
  5. washwashed with water (10 mL)
  6. dry with materialbrine (10 mL), dried over MgSO4
  7. filtrationfiltered
  8. concentrationThe solution was concentrated in vacuo
  9. customThe residue was purified by chromatography on silica gel (EtOAc/heptane=1:3)

Quellen und Nachweise

ORD-Eintrag
ord-a1bef6ae940049f78190d675abecf002
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056865B2

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