Water → 1-Cyclopropyl-6-fluoro-8-chloro-7-[8-(methoxyimino)-2,6-diazaspiro [3,4]oct-6-yl]-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid

HRID 1267615Notes

Reaction equation

HRID 1267615 reaction equation
C(OC([N:8]1[CH2:11][C:10]2([C:15](=[N:16][O:17][CH3:18])[CH2:14][N:13]([C:19]3[C:28]([Cl:29])=[C:27]4[C:22]([C:23](=[O:36])[C:24]([C:33]([OH:35])=[O:34])=[CH:25][N:26]4[CH:30]4[CH2:32][CH2:31]4)=[CH:21][C:20]=3[F:37])[CH2:12]2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.N1C=CC=CC=1.O>ClCCl>[CH:30]1([N:26]2[C:27]3[C:22](=[CH:21][C:20]([F:37])=[C:19]([N:13]4[CH2:14][C:15](=[N:16][O:17][CH3:18])[C:10]5([CH2:11][NH:8][CH2:9]5)[CH2:12]4)[C:28]=3[Cl:29])[C:23](=[O:36])[C:24]([C:33]([OH:35])=[O:34])=[CH:25]2)[CH2:31][CH2:32]1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 539055237-[2-(t-Butoxycarbonyl)-8-(methoxyimino)-2,6-diazaspiro[3,4]oct-6-yl]-1-cyclopropyl-6-fluoro-8-chloro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid

Product 1

HCID 540819591-Cyclopropyl-6-fluoro-8-chloro-7-[8-(methoxyimino)-2,6-diazaspiro [3,4]oct-6-yl]-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-[2-(t-butoxycarbonyl)-8-(methoxyimino)-2,6-diazaspiro[3,4]oct-6-yl]-1-cyclopropyl-6-fluoro-8-chloro-4-oxo-1,4-dihydro-3-quinolinecaboxylic acid was dissolved in 5 ml of dichloromethane and thereto 0.2 ml of trifluoroacetic acid was added dropwise. The mixture was stirred for 18 hours at room temperature, and thereto 10 ml of pyridine and 10 ml of water were added. It was distilled under the reduced pressure to remove dichloromethane and stirred for 1 hour. The precipitated solid was filtered and dried to give the titled compound (67 mg).

Workup

  1. distillationIt was distilled under the reduced pressure
  2. customto remove dichloromethane
  3. stirringstirred for 1 hour
  4. filtrationThe precipitated solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-5374c222dd3649d5ad791128119cf9bb
Source dataset
uspto-grants-2003_04
Patent number
US06552196B2

Reaction notes

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