Trifluoroacetic acid → 7-amino-3-chloro-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one

HRID 222261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 222261
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[O:13])[C:11]3[CH:14]=[C:15]([NH:18]CC4C=CC(OC)=CC=4OC)[CH:16]=[CH:17][C:10]=3[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.FC(F)(F)C(O)=O>CO.ClCCl>[NH2:18][C:15]1[CH:16]=[CH:17][C:10]2[CH:9]=[CH:8][C:5]3=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=[C:4]3[C:12](=[O:13])[C:11]=2[CH:14]=1

Komponenten

5

Edukt 2

HCID 6422Trifluoroacetic acidHCID 159808203-Chloro-7-[[(2,4-dimethoxyphenyl)methyl]amino]-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one

Produkt 1

HCID 159808217-amino-3-chloro-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-chloro-7-[(2,4-dimethoxybenzyl)amino]-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one (1.1 g, 2.7 mmol) was dissolved in 8 mL methanol and 30 mL dichloromethane. Then 10 mL of trifluoroacetic acid was added and the solution was stirred at ambient temperature. After 1 hour, reaction was concentrated, dissolved in 500 mL of ethyl acetate and washed with 200 mL saturated sodium bicarbonate. The organic layer was separated, dried with magnesium sulfate, filtered, and purified by flash column chromatography (0-10% methanol/dichloromethane gradient) and reverse phase HPLC (20-100% acetonitrile/water gradient, 0.1% trifluoroacetic acid modifier) to afford title compound. LRMS (APCI) calculated for C14H10ClN2O [M+H]+, 257.0; found 257.1.

Aufarbeitung

  1. customreaction
  2. concentrationwas concentrated
  3. dissolutiondissolved in 500 mL of ethyl acetate
  4. washwashed with 200 mL saturated sodium bicarbonate
  5. customThe organic layer was separated
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. custompurified by flash column chromatography (0-10% methanol/dichloromethane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-6cd29ab8117447c4bb9c4271d091a5c4
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207186B2

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