(S)-2-{2-[7-chloro-6-(3-cyclopropylureido)-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester → (S)-1-[7-chloro-3-(3,5-dimethylphenyl)-2-oxo-4-(2-piperidin-2-yl-ethoxy)-1,2-dihydroquinolin-6-yl]-3-cyclopropylurea

HRID 1857612Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1857612
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:34])=[C:24]([NH:27][C:28]([NH:30][CH:31]3[CH2:33][CH2:32]3)=[O:29])[CH:25]=2)[NH:20][C:19](=[O:35])[C:18]=1[C:36]1[CH:41]=[C:40]([CH3:42])[CH:39]=[C:38]([CH3:43])[CH:37]=1)=O)(C)(C)C>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>[Cl:34][C:23]1[CH:22]=[C:21]2[C:26]([C:17]([O:16][CH2:15][CH2:14][C@@H:9]3[CH2:10][CH2:11][CH2:12][CH2:13][NH:8]3)=[C:18]([C:36]3[CH:41]=[C:40]([CH3:42])[CH:39]=[C:38]([CH3:43])[CH:37]=3)[C:19](=[O:35])[NH:20]2)=[CH:25][C:24]=1[NH:27][C:28]([NH:30][CH:31]1[CH2:32][CH2:33]1)=[O:29]

Komponenten

4

Edukt 1

HCID 53968811(S)-2-{2-[7-chloro-6-(3-cyclopropylureido)-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 44292939(S)-1-[7-chloro-3-(3,5-dimethylphenyl)-2-oxo-4-(2-piperidin-2-yl-ethoxy)-1,2-dihydroquinolin-6-yl]-3-cyclopropylureaAusbeute 87,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7519AnisoleKatalysatorHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

To a solution of (S)-2-{2-[7-chloro-6-(3-cyclopropylureido)-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (615 mg in 10 mL dry methylene chloride) was added 10 drops of anisole followed by 10 mL of trifluoroacetic acid and the mixture stirred at room temperature. After 1 hour the solvents were removed in vacuo and the resulting residue purified by flash chromatography on silica gel (chloroform:10% ammonium hydroxide in methanol, 90:10) to give the title compound (451 mg).

Aufarbeitung

  1. customAfter 1 hour the solvents were removed in vacuo
  2. customthe resulting residue purified by flash chromatography on silica gel (chloroform:10% ammonium hydroxide in methanol, 90:10)

Quellen und Nachweise

ORD-Eintrag
ord-eafc48d6dd074798bb77b35b1fa243d2
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06147088

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