1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 15859790, 화합물

HRID 1603438

반응식

HRID 1603438 반응식
[C:1]([O:5][C:6]([NH:8][C:9]12[CH2:15][CH2:14][CH:13]1[CH2:12][NH:11][CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:16][C:17]1[C:18](F)=[C:19]([F:34])[CH:20]=[C:21]2[C:26]=1[N:25]([CH:27]1[CH2:29][CH2:28]1)[CH:24]=[C:23]([C:30]([OH:32])=[O:31])[C:22]2=[O:33].C1CCN2C(=NCCC2)CC1>C(#N)C>[C:1]([O:5][C:6]([NH:8][C:9]12[CH2:15][CH2:14][CH:13]1[CH2:12][N:11]([C:18]1[C:17]([Cl:16])=[C:26]3[C:21]([C:22](=[O:33])[C:23]([C:30]([OH:32])=[O:31])=[CH:24][N:25]3[CH:27]3[CH2:29][CH2:28]3)=[CH:20][C:19]=1[F:34])[CH2:10]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 98359418-Chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 15859786tert-Butyl 3-azabicyclo[3.2.0]heptan-1-ylcarbamate

생성물 1

HCID 15859790HCID 15859790, 화합물수율 60.9%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

1.22 g of 1-(t-butoxycarbonylamino)-3-azabicyclo[3.2.0]heptane, 0.96 g of 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid and 0.58 g of 1,8-diazabicyclo[5.4.0]-7-undecene were added to 20 ml of acetonitrile, followed by heating under reflux for 3.5 hours. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (using a 100:1 mixture of chloroform and methanol as the eluent) and recrystallization (from ethyl acetate-diisopropyl ether) to obtain 0.96 g of 7-[1-(t-butoxycarbonylamino)-3-azabicyclo[3.2.0]hept-3-yl]-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (m.p. 200-202° C.).

후처리

  1. temperatureby heating
  2. temperatureunder reflux for 3.5 hours
  3. distillationAfter the solvent was distilled off under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (
  5. additiona 100:1 mixture of chloroform and methanol as the eluent) and
  6. customrecrystallization (from ethyl acetate-diisopropyl ether)

출처 및 근거

ORD 기록
ord-a2656d546ec8415fb777bb28021c474b
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05990106

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