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 428466Notes

Reaction equation

HRID 428466 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 acidYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

150 mg of 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-cf2795c4ae314d64bb6e69f24376c3f6
Source dataset
uspto-grants-2001_11
Patent number
US06313299B1

Reaction notes

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