Octahydropyrrolo[3,4-b]pyrrole → 7-(2,7-Diazabicyclo[3.3.0]octan-7-yl)-1-cyclopropyl-8-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 2209992Notes

Reaction equation

HRID 2209992 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11](F)[C:12]=3[F:14])[C:7](=[O:16])[CH:6]([C:17]([OH:19])=[O:18])[CH2:5]2)[CH2:3][CH2:2]1.[CH:20]12[CH2:27][NH:26][CH2:25][CH:24]1[CH2:23][CH2:22][NH:21]2>CS(C)=O>[CH:20]12[CH2:27][N:26]([C:11]3[C:12]([F:14])=[C:13]4[C:8]([C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5][N:4]4[CH:1]4[CH2:3][CH2:2]4)=[CH:9][CH:10]=3)[CH2:25][CH:24]1[CH2:23][CH2:22][NH:21]2

Participants

4

Reactant 2

HCID 11815320Octahydropyrrolo[3,4-b]pyrroleHCID 193797741-Cyclopropyl-7,8-difluoro-1,3-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 193797587-(2,7-Diazabicyclo[3.3.0]octan-7-yl)-1-cyclopropyl-8-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

620 mg (2.3 mmol) of 1-cyclopropyl-7,8-difluoro-1,3-dihydro-4-oxo-3-quinolinecarboxylic acid together with 315 mg (2.8 mmol) of 2,7-diazabicyclo[3.3.0]octane and 0.51 g (4.6 mmol) of 1,4-diazabicyclo[2.2.21]octane are heated for two hours at 120° C. in 23 ml of dimethyl sulphoxide. All volatile components are removed under a high vacuum, and the residue is stirred thoroughly with acetonitrile and dried at approximately 100° C.

Workup

  1. customAll volatile components are removed under a high vacuum
  2. customdried at approximately 100° C.

Sources & evidence

ORD record
ord-caef96330db24994a6d63e59d974aef5
Source dataset
uspto-grants-1995_10
Patent number
US05457104

Reaction notes

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