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 1094214노트

반응식

HRID 1094214 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6eccc71c0c9342af8413302b321c1ebc
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133882B2

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