1-(7-Bromo-5-pyridin-3-yl-benzothiazol-2-yl)-3-ethyl-urea → 1-[7-(6-Dimethylamino-pyridin-2-yl)-5-pyridin-3-yl-benzothiazol-2-yl]-3-ethyl-urea

HRID 447043Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 447043
Br[C:2]1[C:10]2[S:9][C:8]([NH:11][C:12]([NH:14][CH2:15][CH3:16])=[O:13])=[N:7][C:6]=2[CH:5]=[C:4]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:3]=1.[CH3:23][N:24]([CH3:44])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Sn](CCCC)(CCCC)CCCC)[N:26]=1>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:23][N:24]([CH3:44])[C:25]1[N:26]=[C:27]([C:2]2[C:10]3[S:9][C:8]([NH:11][C:12]([NH:14][CH2:15][CH3:16])=[O:13])=[N:7][C:6]=3[CH:5]=[C:4]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:3]=2)[CH:28]=[CH:29][CH:30]=1

Komponenten

5

Edukt 2

HCID 248642171-(7-Bromo-5-pyridin-3-yl-benzothiazol-2-yl)-3-ethyl-ureaHCID 57813708N,N-Dimethyl-6-(tributylstannyl)pyridin-2-amine

Produkt 1

HCID 578136001-[7-(6-Dimethylamino-pyridin-2-yl)-5-pyridin-3-yl-benzothiazol-2-yl]-3-ethyl-ureaAusbeute 5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 1-(7-bromo-5-pyridin-3-yl-benzothiazol-2-yl)-3-ethyl-urea (0.125 g, 0.33 mmol) in DMF (5 mL) was added dimethyl-(6-tributylstannanyl-pyridin-2-yl)-amine (0.14 g, 0.33 mmol) under nitrogen atmosphere at room temperature. The reaction mixture was then degassed for half an hour followed by the addition of bis(triphenylphosphine)palladium(II) dichloride (0.023 g, 0.033 mmol). The reaction mixture was then again degassed for half an hour and heated at 100° C. for 15 h under nitrogen atmosphere. After the completion of the reaction (TLC monitoring), DMF was distilled off; water was added to the reaction mixture and extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, and evaporated to dryness under reduced pressure. The crude residue was purified by prep HPLC to get the title compound (0.006 g, 5.0%) as off-white solid.

Aufarbeitung

  1. customThe reaction mixture was then degassed for half an hour
  2. customThe reaction mixture was then again degassed for half an hour
  3. customAfter the completion of the reaction (TLC monitoring), DMF
  4. distillationwas distilled off
  5. additionwater was added to the reaction mixture
  6. extractionextracted with ethyl acetate
  7. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  8. customevaporated to dryness under reduced pressure
  9. customThe crude residue was purified by prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-0d3b0de339964f7697c377db49f37a6c
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481544B2

Notizen zur Reaktion

Wird geladen…