1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-(3-t-Butoxycarbonylamino-4-methyl-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 580572Notes

Reaction equation

HRID 580572 reaction equation
[Cl:1][C:2]1[C:3](F)=[C:4]([F:19])[CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([OH:17])=[O:16])[C:7]2=[O:18].[C:21]([O:25][C:26]([NH:28][CH:29]1[CH:33]([CH3:34])[CH2:32][NH:31][CH2:30]1)=[O:27])([CH3:24])([CH3:23])[CH3:22].C1CCN2C(=NCCC2)CC1>C(#N)C>[C:21]([O:25][C:26]([NH:28][CH:29]1[CH:33]([CH3:34])[CH2:32][N:31]([C:3]2[C:2]([Cl:1])=[C:11]3[C:6]([C:7](=[O:18])[C:8]([C:15]([OH:17])=[O:16])=[CH:9][N:10]3[CH:12]3[CH2:14][CH2:13]3)=[CH:5][C:4]=2[F:19])[CH2:30]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]

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 14738853tert-Butyl (4-methylpyrrolidin-3-yl)carbamate

Product 1

HCID 139330937-(3-t-Butoxycarbonylamino-4-methyl-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.5 g), anhydrous acetonitrile (5 ml), 3-t-butoxycarbonylamino-4-methylpyrrolidine (0.5 g) and DBU (0.25 g) was refluxed for an hour. The reacting mixture was concentrated under reduced pressure, to the resulting residue was added acetonitrile-ether (1:1) to crystallize and the precipitate was collected by filtration. This precipitate was recrystallized from dichloromethane-methanol to give the title compound (0.4 g) as pale yellow powder, mp 213°-215° C.

Workup

  1. temperaturewas refluxed for an hour
  2. concentrationThe reacting mixture was concentrated under reduced pressure, to the resulting residue
  3. additionwas added acetonitrile-ether (1:1)
  4. customto crystallize
  5. filtrationthe precipitate was collected by filtration
  6. customThis precipitate was recrystallized from dichloromethane-methanol

Sources & evidence

ORD record
ord-93b09440a0084f409c18a4bd37004c23
Source dataset
uspto-grants-1988_06
Patent number
US04753953

Reaction notes

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