Sodium Bicarbonate → Tert-butyl 4-(3-(3-(6-methylpyridin-3-yl)ureido)phenethyl)piperazine-1-carboxylate

HRID 539729Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539729
[N:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:10])=[N:8][CH:9]=1)=[C:2]=[O:3].C([O-])(O)=O.[Na+].[NH2:16][C:17]1[CH:18]=[C:19]([CH:35]=[CH:36][CH:37]=1)[CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1>CCOC(C)=O>[CH3:10][C:7]1[N:8]=[CH:9][C:4]([NH:1][C:2](=[O:3])[NH:16][C:17]2[CH:18]=[C:19]([CH:35]=[CH:36][CH:37]=2)[CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29])[CH2:26][CH2:27]2)=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 73305055-Isocyanato-2-methylpyridineHCID 57597088Tert-butyl 4-(3-aminophenethyl)piperazine-1-carboxylate2×

Produkt 1

HCID 57597105Tert-butyl 4-(3-(3-(6-methylpyridin-3-yl)ureido)phenethyl)piperazine-1-carboxylateAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 4-(3-aminophenethyl)piperazine-1-carboxylate (7D, 1.0 eq) in THF (about 0.3 M 7D in THF) was added 5-isocyanato-2-methylpyridine (1.0 eq) dropwise. The resulting reaction mixture was stirred for 2 h. To the reaction mixture was added saturated aq. NaHCO3. The mixture was diluted with EtOAc, and the layers were separated. The organic layer was washed twice with saturated aq. NaHCO3 and once with brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. Purification over silica gel using 5-12% MeOH/CH2Cl2 as the gradient eluant provided tert-butyl 4-(3-(3-(6-methylpyridin-3-yl)ureido)phenethyl)piperazine-1-carboxylate (7E, 63%).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customthe layers were separated
  3. washThe organic layer was washed twice with saturated aq. NaHCO3 and once with brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification over silica gel using 5-12% MeOH/CH2Cl2 as the gradient eluant

Quellen und Nachweise

ORD-Eintrag
ord-52cddbaee2324b1dbb8c0cb3180ed7fe
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871769B2

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