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

HRID 421815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 421815
[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 Na2 SO4, 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. customThe organic layer was dried over Na2 SO4
  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-fa341948b40c477aac7c6c4b77ca6cb0
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101617B2

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