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

HRID 1603438Notes

Reaction equation

HRID 1603438 reaction equation
[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]

Participants

5

Reactant 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

Product 1

HCID 15859790HCID 15859790, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.).

Workup

  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)

Sources & evidence

ORD record
ord-a2656d546ec8415fb777bb28021c474b
Source dataset
uspto-grants-1999_11
Patent number
US05990106

Reaction notes

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