Ammonium Chloride → Diethyl[[7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl](hydroxy)methyl]phosphonate

HRID 469242노트

반응식

HRID 469242 반응식
[CH:1]1([NH:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:25])[C:13]([CH:23]=[O:24])=[CH:14][N:15]3[CH:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:10][C:9]=2[F:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[P:27]([O-:34])([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30].C1CCN2C(=NCCC2)CC1.[Cl-].[NH4+]>ClCCl>[CH2:29]([O:28][P:27]([CH:23]([C:13]1[C:12](=[O:25])[C:11]2[C:16](=[CH:17][C:8]([NH:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[C:9]([F:26])[CH:10]=2)[N:15]([CH:18]([CH2:19][CH3:20])[CH2:21][CH3:22])[CH:14]=1)[OH:24])(=[O:34])[O:31][CH2:32][CH3:33])[CH3:30]

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 3780918DiethylphosphiteHCID 86633064HCID 86633064, 화합물

생성물 1

HCID 86633063Diethyl[[7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl](hydroxy)methyl]phosphonate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a 5.0 ml dichloromethane solution of 500 mg of 7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carbaldehyde were added 0.23 ml of diethyl phosphite and 0.22 ml of 1,8-diazabicyclo[5.4.0]-7-undecene at −40° C., followed by overnight stirring at room temperature. Aqueous saturated ammonium chloride was added to the reaction mixture, followed by extraction with chloroform and then washing with aqueous saturated sodium chloride. After drying over anhydrous sodium sulfate and subsequent evaporation under a reduced pressure, the resulting residue was purified by silica gel column chromatography to obtain 400 mg of diethyl[[7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl](hydroxy)methyl]phosphonate.

후처리

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

출처 및 근거

ORD 기록
ord-a73c18bed3974391bfc9dd971d545597
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629126B2

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