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

HRID 2209991Notes

Reaction equation

HRID 2209991 reaction equation
[Cl:1][C:2]1[C:3](F)=[CH:4][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].[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:3]3[C:2]([Cl:1])=[C:11]4[C:6]([C:7](=[O:18])[C:8]([C:15]([OH:17])=[O:16])=[CH:9][N:10]4[CH:12]4[CH2:14][CH2:13]4)=[CH:5][CH:4]=3)[CH2:25][CH:24]1[CH2:23][CH2:22][NH:21]2

Participants

4

Reactant 2

HCID 11815320Octahydropyrrolo[3,4-b]pyrroleHCID 183332011-Cyclopropyl-1,4-dihydro-7-fluoro-8-chloro-4-oxo-quinoline-3-carboxylic Acid

Product 1

HCID 193797997-(2,7-Diazabicyclo[3.3.0]octan-7-yl)-8-chloro-1-cyclopropyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

650 mg (2.3 mmol) of 8-chloro-l-cyclopropyl-7-fluoro-1,4 -dihydro-4 -oxo-3 -quinolinecarboxylic acid together with 315 mg (2.8 retool) of 2,7-diazabicyclo[3.3.0]octane and 510 mg (4.6 mmol) of 1,4-diazabicyclo[2.2.21]octane are heated for six 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-08cd4cb2c8fa4ce7a0454ce8bb20e8dc
Source dataset
uspto-grants-1995_10
Patent number
US05457104

Reaction notes

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