Ammonium formate → 3-[3-[[1-(2-Hydroxyphenyl)-1-methylethyl]amino]-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzoic acid methyl ester

HRID 1697333Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1697333
Br[C:2]1[N:3]=[C:4]([NH:20][C:21]([CH3:37])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29]CC2C=CC=CC=2)[CH3:22])[C:5](=[O:19])[N:6]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=2[CH3:18])[C:11]([O:13][CH3:14])=[O:12])[CH:7]=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH3:14][O:13][C:11](=[O:12])[C:10]1[CH:15]=[CH:16][C:17]([CH3:18])=[C:8]([N:6]2[CH:7]=[CH:2][N:3]=[C:4]([NH:20][C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[OH:29])([CH3:37])[CH3:22])[C:5]2=[O:19])[CH:9]=1

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 666898163-[5-Bromo-3-[[1-methyl-1-[2-(phenylmethoxy)phenyl]ethyl]amino]-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzoic acid methyl ester

Produkt 1

HCID 666901483-[3-[[1-(2-Hydroxyphenyl)-1-methylethyl]amino]-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzoic acid methyl esterAusbeute 100,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To 3-[5-bromo-3-[[1-methyl-1-[2-(phenylmethoxy)phenyl]ethyl]amino]-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzoic acid, methyl ester (Example 220a, 2 g) in ethanol (50 mL) was added ammonium formate (3.14 g) and 10% Pd/C (0.378 g) and the reaction heated at 75° C. for 1 h. The reaction was filtered through celite and the filtrate concentrated in vacuo. The reaction mixture was diluted with water (250 mL) and extracted with dichloromethane (250 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give the subtitle compound (1.410 g).

Aufarbeitung

  1. filtrationThe reaction was filtered through celite
  2. concentrationthe filtrate concentrated in vacuo
  3. additionThe reaction mixture was diluted with water (250 mL)
  4. extractionextracted with dichloromethane (250 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-eeaef9f8edca4dfa8643586b8ffa479a
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163905B2

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