Ammonium Chloride → 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-N-methoxy-N-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide

HRID 1094161ノート

反応式

HRID 1094161 の反応式
ClC(OCC(C)C)=O.[CH:9]1([NH:15][C:16]2[CH:25]=[C:24]3[C:19]([C:20](=[O:34])[C:21]([C:31]([OH:33])=O)=[CH:22][N:23]3[CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:18][C:17]=2[F:35])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.Cl.[CH3:37][NH:38][O:39][CH3:40].[Cl-].[NH4+]>C(Cl)(Cl)Cl.ClCCl.C(N(CC)CC)C>[CH:9]1([NH:15][C:16]2[CH:25]=[C:24]3[C:19]([C:20](=[O:34])[C:21]([C:31]([N:38]([O:39][CH3:40])[CH3:37])=[O:33])=[CH:22][N:23]3[CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:18][C:17]=2[F:35])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1

参加物

8

反応物 4

HCID 25517Ammonium ChlorideHCID 62365Isobutyl chloroformateHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 666369197-(Cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

生成物 1

HCID 866330497-(cyclohexylamino)-1-cyclopentyl-6-fluoro-N-methoxy-N-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide収率 85.2%

試薬・触媒・溶媒 3

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

反応条件

温度
0 °C

実験手順

0.87 ml of triethylamine and 0.4 ml of isobutyl chloroformate were added to a 20 ml of dichloromethane solution of 1.0 g of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid at 0° C., followed by stirring at 0° C. for 30 minutes. Then, 315 mg of N,O-dimethylhydroxylamine hydrochloride was added thereto, followed by stirring at room temperature for 1 hour. Chloroform and aqueous saturated ammonium chloride were added to the reaction mixture, the layers were separated, and the organic layer was washed with aqueous saturated so iumchloride. After drying over anhydrous sodium sulfate and subsequent filtration, the solvent was evaporated under a reduced pressure. By purifying the resulting residue by silica gel column chromatography, 950 mg of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-N-methoxy-N-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide was obtained.

後処理

  1. stirringby stirring at room temperature for 1 hour
  2. customthe layers were separated
  3. washthe organic layer was washed with aqueous saturated so iumchloride
  4. dry with materialAfter drying over anhydrous sodium sulfate and subsequent filtration
  5. customthe solvent was evaporated under a reduced pressure
  6. customBy purifying the resulting residue by silica gel column chromatography

出典と根拠

ORDレコード
ord-1378075dda3240bdaefe91d15d7cbcd1
出典データセット
uspto-grants-2012_03
特許番号
US08133882B2

反応ノート

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