1,8-Diazabicyclo(5.4.0)undec-7-ene → 9-Fluoro-2,3-dihydro-3-methyl-10-(7-methyl-2,7-diazaspiro[4.4]non-2-yl)-7-oxo-7H-pyrido[1,2,3-de]1,4-benzoxazine-6-carboxylic acid

HRID 622491Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 622491
Cl.Cl.[CH3:3][N:4]1[CH2:8][CH2:7][C:6]2([CH2:12][CH2:11][NH:10][CH2:9]2)[CH2:5]1.N12CCCN=C1CCCCC2.[F:24][C:25]1[C:26](F)=[C:27]2[O:32][CH2:31][CH:30]([CH3:33])[N:29]3[CH:34]=[C:35]([C:40]([OH:42])=[O:41])[C:36](=[O:39])[C:37]([CH:38]=1)=[C:28]23>C(#N)C>[F:24][C:25]1[C:26]([N:10]2[CH2:11][CH2:12][C:6]3([CH2:7][CH2:8][N:4]([CH3:3])[CH2:5]3)[CH2:9]2)=[C:27]2[O:32][CH2:31][CH:30]([CH3:33])[N:29]3[CH:34]=[C:35]([C:40]([OH:42])=[O:41])[C:36](=[O:39])[C:37]([CH:38]=1)=[C:28]23

Komponenten

5

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5342788,9-Difluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acidHCID 134918062-Methyl-2,7-diazaspiro[4.4]nonane--hydrogen chloride (1/2)

Produkt 1

HCID 137728419-Fluoro-2,3-dihydro-3-methyl-10-(7-methyl-2,7-diazaspiro[4.4]non-2-yl)-7-oxo-7H-pyrido[1,2,3-de]1,4-benzoxazine-6-carboxylic acidAusbeute 60,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A suspension of 0.42 g (1.97 mmol) 2-methyl-2,7-diazaspiro[4.4]nonane dihydrochloride in 25 ml acetonitrile was treated with 0.85 g (5.80 mmol) 1,8-diazabicyclo[5.4.0]undec-7-ene and 0.52 g (1.85 mmol) 9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]1,4-benzoxazine-6-carboxylic acid was added. The mixture was stirred carboxylic acid was added. The mixture was stirred two hours at room temperature and then refluxed overnight. The product which crystallized on cooling was filtered, washed with acetonitrile and recrystallized from acetonitrile to afford 0.45 g of the title compound, mp 227°-230° C. (dec). Analysis calculated for C21H22N3FO4 :

Aufarbeitung

  1. additionwas added
  2. additionwas added
  3. temperaturerefluxed overnight
  4. customThe product which crystallized
  5. temperatureon cooling
  6. filtrationwas filtered
  7. washwashed with acetonitrile
  8. customrecrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-772d8f2af6ad4b72ad80ebd71efaae5d
Quelldatensatz
uspto-grants-1988_09
Patentnummer
US04771054

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