Acetonitrile → 10-[3-[(ethylamino) methyl]-1-pyrrolidinyl]-9-fluoro-2,3-dihydro-3-ethyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid

HRID 622485

Reaktionsgleichung

Reaktionsgleichung von HRID 622485
[F:1][C:2]1[C:3](F)=[C:4]2[O:9][CH2:8][CH:7]([CH3:10])[N:6]3[CH:11]=[C:12]([C:17]([OH:19])=[O:18])[C:13](=[O:16])[C:14]([CH:15]=1)=[C:5]23.[CH2:21]([NH:23][CH2:24][CH:25]1[CH2:29][CH2:28][NH:27][CH2:26]1)[CH3:22].[C:30](#N)C>>[CH2:21]([NH:23][CH2:24][CH:25]1[CH2:29][CH2:28][N:27]([C:3]2[C:2]([F:1])=[CH:15][C:14]3[C:13](=[O:16])[C:12]([C:17]([OH:19])=[O:18])=[CH:11][N:6]4[CH:7]([CH2:10][CH3:30])[CH2:8][O:9][C:4]=2[C:5]=34)[CH2:26]1)[CH3:22]

Komponenten

4

Edukt 3

HCID 6342AcetonitrileHCID 5342788,9-Difluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acidHCID 13491786Ethyl-pyrrolidin-3-ylmethyl-amine

Produkt 1

HCID 1385364010-[3-[(ethylamino) methyl]-1-pyrrolidinyl]-9-fluoro-2,3-dihydro-3-ethyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid

Versuchsvorschrift

0.75 g (2.7 mmole) of 9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid, 40 ml acetonitrile and 1.03 g (8.00 mmole) of N-ethyl-3-pyrrolidinemethanamine were refluxed overnight. The reaction mixture was cooled in an ice bath and then filtered. The precipitate was washed with ethanol/ether (4:1), and then with ether until dry to give 0.86 g of 10-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-9-fluoro-2,3-dihydro-3-ethyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid, mp 221°-224° C.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. filtrationfiltered
  3. washThe precipitate was washed with ethanol/ether (4:1)
  4. dry with materialwith ether until dry

Quellen und Nachweise

ORD-Eintrag
ord-39a4e81714754a999c83cf074f5c41c5
Quelldatensatz
uspto-grants-1988_09
Patentnummer
US04771054

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