Acetonitrile → 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-quinolinecarboxylic acid

HRID 1267608Notes

Reaction equation

HRID 1267608 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[Cl:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.[CH3:21][O:22][N:23]=[C:24]1[C:28]2([CH2:31][N:30]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:29]2)[CH2:27][NH:26][CH2:25]1.C(#N)C>C(N(CC)CC)C>[C:35]([O:34][C:32]([N:30]1[CH2:31][C:28]2([C:24](=[N:23][O:22][CH3:21])[CH2:25][N:26]([C:11]3[C:12]([Cl:14])=[C:13]4[C:8]([C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5][N:4]4[CH:1]4[CH2:3][CH2:2]4)=[CH:9][C:10]=3[F:16])[CH2:27]2)[CH2:29]1)=[O:33])([CH3:38])([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 98359418-Chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 545476562,6-Diazaspiro[3.4]octane-2-carboxylic acid, 8-(methoxyimino)-, 1,1-dimethylethyl ester

Product 1

HCID 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 acidYield 31.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

1-cyclopropyl-6,7-difluoro-8-chloro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid, 530 mg of t-butyl 8-(methoxyimino)-2,6-diazaspiro[3,4]octane-2-carboxylate and 2 g of AmberliteR IRA-420 were added to 10 ml of acetonitrile and thereto 1 ml of triethylamine was added by dropping. The resulting mixture was refluxed for 72 hours and then the resulting solid was filtered off. The filtrate was concentrated under the reduced pressure and thereto 10 ml of ethylacetate was added and the resulting solution was stirred for 4 hours. The precipitated solid was filtered and dried to give 169 mg of the titled compound (yield: 31.4%).

Workup

  1. temperatureThe resulting mixture was refluxed for 72 hours
  2. filtrationthe resulting solid was filtered off
  3. concentrationThe filtrate was concentrated under the reduced pressure
  4. addition10 ml of ethylacetate was added
  5. filtrationThe precipitated solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-dbd3abc4d4f7418bb7748bd93d90f811
Source dataset
uspto-grants-2003_04
Patent number
US06552196B2

Reaction notes

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