Potassium Phosphate, Tribasic → Pyridin-3-ylmethyl{[4-({[6-chloro-3-({[(1,1-dimethylethyl)oxy]carbonyl}amino)pyridin-2-yl]amino}carbonyl)phenyl]methyl}carbamate

HRID 1256658Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1256658
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][O:8][C:9](=[O:21])[NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([NH2:20])=[O:19])=[CH:14][CH:13]=2)[CH:2]=1.CC([N:26]([C:30]1[C:31](Cl)=[N:32][C:33]([Cl:36])=[CH:34][CH:35]=1)[C:27](=[O:29])[O-:28])(C)C.[CH3:38][C:39]1(C)[C:65]2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=C[C:40]1=2.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C(OCC)(=O)C.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]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][O:8][C:9](=[O:21])[NH:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]([NH:20][C:31]3[C:30]([NH:26][C:27]([O:28][C:39]([CH3:65])([CH3:40])[CH3:38])=[O:29])=[CH:35][CH:34]=[C:33]([Cl:36])[N:32]=3)=[O:19])=[CH:16][CH:17]=2)[CH:2]=1

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 57745589HCID 57745589, VerbindungHCID 1317306211,1-Dimethylethyl(2,6-dichloropyridin-3-yl)carbamate

Produkt 1

HCID 59627859Pyridin-3-ylmethyl{[4-({[6-chloro-3-({[(1,1-dimethylethyl)oxy]carbonyl}amino)pyridin-2-yl]amino}carbonyl)phenyl]methyl}carbamate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of pyridin-3-ylmethyl{[4-(aminocarbonyl)phenyl]methyl}carbamate (0.2 g, 0.70 mmol), 1,1-dimethylethyl(2,6-dichloropyridin-3-yl)carbamate (0.18 g, 0.70 mmol), Pd2(dba)3 (32 mg, 0.035 mmol), Xantphos (41 mg, 0.07 mmol) and K3PO4 (0.45 g, 2.1 mmol) in dioxane (3 mL) was degassed with nitrogen, sealed and heated to 100° C. for 14 hours. The reaction was diluted with ethyl acetate (50 mL), filtered through Celite and evaporated in vacuo. Purification by flash chromatography (0-3% methanol/DCM) gave pyridin-3-ylmethyl{[4-({[6-chloro-3-({[(1,1-dimethylethyl)oxy]carbonyl}amino)pyridin-2-yl]amino}carbonyl)phenyl]methyl}carbamate. MS: cal'd 512 (MH+), exp 512 (MH+).

Aufarbeitung

  1. customsealed
  2. filtrationfiltered through Celite
  3. customevaporated in vacuo
  4. customPurification by flash chromatography (0-3% methanol/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-a860497769c34f648926b060c6442e18
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461189B2

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