Potassium Phosphate, Tribasic → Pyridin-3-ylmethyl{4-[({3-[(tert-butoxycarbonyl)amino]-6-phenylpyridin-2-yl}amino)carbonyl]benzyl}carbamate

HRID 1256669Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1256669
[NH2:1][C:2]([C:4]1[CH:21]=[CH:20][C:7]([CH2:8][NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:6][CH:5]=1)=[O:3].[C:22]([O:26][C:27]([N:29]([C:37]1[C:38](Cl)=[N:39][C:40]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:41][CH:42]=1)C(OC(C)(C)C)=O)=[O:28])([CH3:25])([CH3:24])[CH3:23].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(O)=O.[Na+].CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[N:15]1[CH:16]=[CH:17][CH:18]=[C:13]([CH2:12][O:11][C:10](=[O:19])[NH:9][CH2:8][C:7]2[CH:20]=[CH:21][C:4]([C:2]([NH:1][C:38]3[C:37]([NH:29][C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:28])=[CH:42][CH:41]=[C:40]([C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)[N:39]=3)=[O:3])=[CH:5][CH:6]=2)[CH:14]=1

Komponenten

9

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 57745583Di-tert-butyl(2-chloro-6-phenylpyridin-3-yl)imidodicarbonateHCID 57745589HCID 57745589, Verbindung

Produkt 1

HCID 59627858Pyridin-3-ylmethyl{4-[({3-[(tert-butoxycarbonyl)amino]-6-phenylpyridin-2-yl}amino)carbonyl]benzyl}carbamate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Pyridin-3-ylmethyl [4-(aminocarbonyl)benzyl]carbamate (0.35 g, 1.24 mmol), di-tert-butyl(2-chloro-6-phenylpyridin-3-yl)imidodicarbonate (0.5 g, 1.24 mmol), Xanthphos (0.07 g, 0.12 mmol), potassium phosphate, tribasic (0.79 g, 3.70 mmol), and Pd2(dba)3 (0.57 g, 0.06 mmol) were combined in a 20 mL microwave vial and dioxane was added. The mixture was degassed for 20 mins, then sealed and heated to 100° C. overnight. Reaction was not complete and was continued another 24 h, for a total of 48 h at 100° C. The reaction was cooled to RT, diluted with saturated NaHCO3 solution and EtOAc, and the layers were separated. The water layer was extracted with EtOAc (2×100 mL). The combined organic fractions were washed with brine, dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified on a Biotage 65i column to yield pyridin-3-ylmethyl{4-[({3-[(tert-butoxycarbonyl)amino]-6-phenylpyridin-2-yl}amino)carbonyl]benzyl}carbamate. MS: cal'd 554 (MH+), exp 554 (MH+).

Aufarbeitung

  1. customThe mixture was degassed for 20 mins
  2. customsealed
  3. customReaction
  4. temperatureThe reaction was cooled to RT
  5. customthe layers were separated
  6. extractionThe water layer was extracted with EtOAc (2×100 mL)
  7. washThe combined organic fractions were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customThe residue was purified on a Biotage 65i column

Quellen und Nachweise

ORD-Eintrag
ord-d07a29c446fe44f388539324b0c293d6
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461189B2

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