Hydrochloric Acid → 2-{[7-(Cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]methyl}-1,2,4-oxadiazolidine-3,5-dione

HRID 469256ノート

反応式

HRID 469256 の反応式
[C:1](=[O:6])=[N:2][C:3](Cl)=[O:4].[CH:7]1([NH:13][C:14]2[CH:23]=[C:22]3[C:17]([C:18](=[O:32])[C:19]([CH2:29][NH:30][OH:31])=[CH:20][N:21]3[CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:16][C:15]=2[F:33])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.Cl>C1COCC1>[CH:7]1([NH:13][C:14]2[CH:23]=[C:22]3[C:17]([C:18](=[O:32])[C:19]([CH2:29][N:30]4[C:3](=[O:4])[NH:2][C:1](=[O:6])[O:31]4)=[CH:20][N:21]3[CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:16][C:15]=2[F:33])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 119708Isocyanatocarbonyl chlorideHCID 866330717-(cyclohexylamino)-1-cyclopentyl-6-fluoro-3-[(hydroxyamino)methyl]quinolin-4(1H)-one

生成物 1

HCID 666369432-{[7-(Cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]methyl}-1,2,4-oxadiazolidine-3,5-dione

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

0.14 ml of N-(chlorocarbonyl) isocyanate was added dropwise at −50° C. to a 4 ml THF solution of 110 mg of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-3-[(hydroxyamino)methyl]quinolin-4(1H)-one, followed by stirring at room temperature for 1 hour. 1 M hydrochloric acid was added to the reaction mixture, followed by extraction with chloroform and washing with aqueous saturated sodium chloride. After drying over anhydrous sodium sulfate, the solvent was evaporated under a reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain 45 mg of 2-{[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]methyl}-1,2,4-oxadiazolidine-3,5-dione.

後処理

  1. extractionfollowed by extraction with chloroform
  2. washwashing with aqueous saturated sodium chloride
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. customthe solvent was evaporated under a reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-d82decd8c2ff4e959d88356f5f5d8121
出典データセット
uspto-grants-2014_01
特許番号
US08629126B2

反応ノート

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