Acetonitrile → 7-[2-(t-Butoxycarbonyl)-8-(methoxyimino)-2,6-diazaspiro[3,4]oct-6-yl]-1-cyclopropyl-5-amino-6,8-difluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid

HRID 428461

Reaktionsgleichung

Reaktionsgleichung von HRID 428461
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([NH2:17])[C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.[CH3:22][O:23][N:24]=[C:25]1[C:29]2([CH2:32][N:31]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:30]2)[CH2:28][NH:27][CH2:26]1.C(#N)C.C(N(CC)CC)C>CN(C)C=O>[C:36]([O:35][C:33]([N:31]1[CH2:32][C:29]2([C:25](=[N:24][O:23][CH3:22])[CH2:26][N:27]([C:11]3[C:12]([F:14])=[C:13]4[C:8]([C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5][N:4]4[CH:1]4[CH2:2][CH2:3]4)=[C:9]([NH2:17])[C:10]=3[F:16])[CH2:28]2)[CH2:30]1)=[O:34])([CH3:39])([CH3:38])[CH3:37]

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 545476562,6-Diazaspiro[3.4]octane-2-carboxylic acid, 8-(methoxyimino)-, 1,1-dimethylethyl ester

Produkt 1

HCID 543496637-[2-(t-Butoxycarbonyl)-8-(methoxyimino)-2,6-diazaspiro[3,4]oct-6-yl]-1-cyclopropyl-5-amino-6,8-difluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acidAusbeute 31,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

750 mg of 1-cyclopropyl-5-amino-6,7,8-trifluoro-4-oxo-1,4-dihydro-3-quinoline-carboxylic acid, 1.05 g of t-butyl 8-(methoxyimino)-2,6-diazaspiro[3,4]octane-2-carboxylate and 4 g of Amberlite® IRA-420 were added to 20 ml of acetonitrile and thereto 2 ml of triethylamine was added by dropping. The mixture was refluxed for 5 days and then 2 ml of dimethylformamide was added thereto. The resulting mixture was stirred for 1 hour and thus precipitated solid was filtered off. The filtrate was concentrated under the reduced pressure and then to the resulting residue 10 ml of acetonitrile was added and stirred for 1 hour. The precipitated solid was filtered and dried to give 420 mg of the titled compound(yield: 30.9%).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 5 days
  2. filtrationthus precipitated solid was filtered off
  3. concentrationThe filtrate was concentrated under the reduced pressure
  4. additionto the resulting residue 10 ml of acetonitrile was added
  5. stirringstirred for 1 hour
  6. filtrationThe precipitated solid was filtered
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d7fd68198c9d4954a1470470f7d25f9d
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313299B1

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