Acetonitrile → HCID 53801097, compound

HRID 1267612Notes

Reaction equation

HRID 1267612 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([NH2:17])[C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.[CH2:22]([O:24][N:25]=[C:26]1[C:30]2([CH2:33][N:32]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:31]2)[CH2:29][NH:28][CH2:27]1)[CH3:23].C(#N)C>C(N(CC)CC)C>[C:37]([O:36][C:34]([N:32]1[CH2:33][C:30]2([C:26](=[N:25][O:24][CH2:22][CH3:23])[CH2:27][N:28]([C:11]3[C:12]([F:14])=[C:13]4[C:8]([C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5][N:4]4[CH:1]4[CH2:3][CH2:2]4)=[C:9]([NH2:17])[C:10]=3[F:16])[CH2:29]2)[CH2:31]1)=[O:35])([CH3:40])([CH3:39])[CH3:38]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 54099510HCID 54099510, compound

Product 1

HCID 53801097HCID 53801097, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

1-cyclopropyl-5-amino-6,7,8-trifluoro-4-oxo-1,4-dihydro-3-quinoline-carboxylic acid, 680 mg of t-butyl 8-(ethoxyimino)-2,6-diazaspiro[3,4]octane-2-carboxylate and 2 g of AmberliteR IRA-420 were added to 15 ml of acetonitrile and thereto 1.5 ml of triethylamine was dropped and the resulting mixture was refluxed for 5 days and filtered. The filtrate was concentrated under the reduced pressure and to the resulting residue 10 ml of isopropanol was added and the resulting solution was stirred for 1 hour at room temperature. The precipitated solid was filtered and dried to give 380 mg of the titled compound (yield: 51.1%).

Workup

  1. temperaturethe resulting mixture was refluxed for 5 days
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under the reduced pressure and to the resulting residue 10 ml of isopropanol
  4. additionwas added
  5. filtrationThe precipitated solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-17bb2738c5e5470d8fb2be7ebd806de1
Source dataset
uspto-grants-2003_04
Patent number
US06552196B2

Reaction notes

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