1-Chloroethyl chloroformate → 7-[4-(1-Chloro-2-methylamino-ethylidene)-piperidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid trifluoroacetic acid salt

HRID 15505

Reaktionsgleichung

Reaktionsgleichung von HRID 15505
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:8]([N:15]([CH2:17][C:18](=[C:20]1[CH2:25][CH2:24][N:23]([C:26]2[C:35]([O:36][CH3:37])=[C:34]3[C:29]([C:30](=[O:44])[C:31]([C:41]([OH:43])=[O:42])=[CH:32][N:33]3[CH:38]3[CH2:40][CH2:39]3)=[CH:28][C:27]=2[F:45])[CH2:22][CH2:21]1)[Cl:19])C)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClCCCl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:19][C:18](=[C:20]1[CH2:25][CH2:24][N:23]([C:26]2[C:35]([O:36][CH3:37])=[C:34]3[C:29]([C:30](=[O:44])[C:31]([C:41]([OH:43])=[O:42])=[CH:32][N:33]3[CH:38]3[CH2:40][CH2:39]3)=[CH:28][C:27]=2[F:45])[CH2:22][CH2:21]1)[CH2:17][NH:15][CH3:8]

Komponenten

4

Edukt 2

HCID 5213051-Chloroethyl chloroformateHCID 686897667-[4-[2-(n-Benzyl-n-methylamino)-1-chloroethylidene]piperidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid trifluoroacetic acid salt

Produkt 1

HCID 686923157-[4-(1-Chloro-2-methylamino-ethylidene)-piperidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid trifluoroacetic acid saltAusbeute 27,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

A solution of 161 (160 mg, 0.24 mmol) was dissolved in 1,2-dichloroethane (4 mL) and was treated with 1-chloroethyl chloroformate (0.8 mL, 7.3 mmol) under nitrogen. After 5 min, the reaction mixture was warmed to reflux temperature and the reaction mixture was allowed to stir for 3 h. The resulting mixture was allowed to cool to room temperature, and then it was concentrated in vacuo. The residue was dissolved in tetrahydrofuran (5 mL), adjusted to pH>7 by the addition of NaHCO3 and water at room temperature and stirred overnight. The resulting mixture was concentrated in vacuo and the residue purified by HPLC (reverse phase C-18 column, 35-90% acetonitrile/water containing 0.1% trifluoroacetic acid) to afford the trifluoroacetic acid salt of 72 (37 mg, 27%) as a yellow solid. MS 450 (M+H).

Aufarbeitung

  1. temperaturethe reaction mixture was warmed
  2. temperatureto reflux temperature
  3. concentrationit was concentrated in vacuo
  4. dissolutionThe residue was dissolved in tetrahydrofuran (5 mL)
  5. additionadjusted to pH>7 by the addition of NaHCO3 and water at room temperature
  6. stirringstirred overnight
  7. concentrationThe resulting mixture was concentrated in vacuo
  8. customthe residue purified by HPLC (reverse phase C-18 column, 35-90% acetonitrile/water containing 0.1% trifluoroacetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-660a94f0327642f5a628d428f99bb177
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732612B2

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