Dichloromethane → N-(4-Methoxy-phenyl)-N-(carboxypropyl-sulfonyl)-thieno[2,3-b]quinoline-4-carboxamide

HRID 641140Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 641140
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([S:25]([CH2:28][CH2:29][CH2:30][C:31]([O:33]C(C)(C)C)=[O:32])(=[O:27])=[O:26])[C:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[C:14]3[S:22][CH:23]=[CH:24][C:13]=23)=[O:11])=[CH:5][CH:4]=1.C(Cl)Cl>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]([S:25]([CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])(=[O:26])=[O:27])[C:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[C:14]3[S:22][CH:23]=[CH:24][C:13]=23)=[O:11])=[CH:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 6344DichloromethaneHCID 68638513N-(4-methoxy-phenyl)-N-(tert-butyl-oxycarbonylpropyl-sulfonyl)-thieno[2,3-b]quinoline-4-carboxamide

Produkt 1

HCID 68637627N-(4-Methoxy-phenyl)-N-(carboxypropyl-sulfonyl)-thieno[2,3-b]quinoline-4-carboxamideAusbeute 104,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

80 mg (0.13 mmol) N-(4-Methoxy-phenyl)-N-(tert-butyl-oxycarbonylpropyl-sulfonyl)-thieno-[2,3-b]quinoline-4-carboxamide 16 were dissolved in 1.2 mL trifluoroacetic acid and stirred for 30 minutes at room temperature. 50 mg of silica gel and 10 mL of methylene chloride were added and the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel (eluent: methylene chloride/diethylether 6:4+0.1% trifluoroacetic acid). Evaporation of the appropriate fractions gave 66 mg of the desired product 17.

Aufarbeitung

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was purified by chromatography on silica gel (eluent: methylene chloride/diethylether 6:4+0.1% trifluoroacetic acid)
  3. customEvaporation of the appropriate fractions

Quellen und Nachweise

ORD-Eintrag
ord-28d3146ff9424d2680cb90e79251ac22
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07695980B2

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