3-(Benzyloxy)-1-methyl-5-(3-phenyl-1H-pyrazol-1-yl)pyridin-2(1H)-one → 3-hydroxy-1-methyl-5-(3-phenyl-1H-pyrazol-1-yl)pyridin-2(1H)-one

HRID 625948

Reaktionsgleichung

Reaktionsgleichung von HRID 625948
C([O:8][C:9]1[C:10](=[O:27])[N:11]([CH3:26])[CH:12]=[C:13]([N:15]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:16]2)[CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[C:10](=[O:27])[N:11]([CH3:26])[CH:12]=[C:13]([N:15]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:16]2)[CH:14]=1

Komponenten

4

Edukt 1

HCID 674189523-(Benzyloxy)-1-methyl-5-(3-phenyl-1H-pyrazol-1-yl)pyridin-2(1H)-one

Produkt 1

HCID 533798143-hydroxy-1-methyl-5-(3-phenyl-1H-pyrazol-1-yl)pyridin-2(1H)-oneAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

3-(Benzyloxy)-1-methyl-5-(3-phenyl-1H-pyrazol-1-yl)pyridin-2(1H)-one (33 mg, 0.092 mmol) was hydrogenated (balloon) with 10% Pd/C (10 mg, 9.40 μmol) in MeOH (1 mL) at R.T. After stirring overnight the mixture was filtered using a 0.45 μm PTFE syringe filter and concentrated. The crude material was purified by preparative reversed-phase HPLC (20×150 mm Waters Sunfire (0.1% TFA), 5-60% CH3CN/water over 20 min at 20 mL/ruin) to give the title compound (10 mg, 41%) as an off-white solid. 1H NMR (500 MHz, CDCl3): δ 7.86 (d, J=7.6 Hz, 2 H); 7.71 (s, 1 H); 7.49-7.39 (m, 3 H); 7.35 (m, 1 H); 7.21 (s, 1 H); 6.95 (bs, 1 H); 6.75 (d, J=2.4 Hz, 1 H); 3.71 (s, 3 H). HRMS (ES) calc (M+H)+=268.1081, found 268.1071.

Aufarbeitung

  1. customat R.T
  2. filtrationwas filtered
  3. filtrationfilter
  4. concentrationconcentrated
  5. customThe crude material was purified by preparative reversed-phase HPLC (20×150 mm Waters Sunfire (0.1% TFA), 5-60% CH3CN/water over 20 min at 20 mL/ruin)

Quellen und Nachweise

ORD-Eintrag
ord-cdd272c1b653412cb2aa933def5a1a3c
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309199B2

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