Hydrochloric Acid → 5-Amino-7-(3-aminopiperidin-1-yl)-1-cyclopropyl-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 729067Notes

Reaction equation

HRID 729067 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.[ClH:22].[NH2:23][CH:24]1[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]1.C(N(CC)CC)C.Cl>C(#N)C.C(O)(C)C>[ClH:22].[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:26]2[CH2:27][CH2:28][CH2:29][CH:24]([NH2:23])[CH2:25]2)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 19691262Piperidin-3-amine--hydrogen chloride (1/1)

Product 2

HCID 313Hydrochloric AcidHCID 1480775-Amino-7-(3-aminopiperidin-1-yl)-1-cyclopropyl-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 36.4%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6342AcetonitrileSolvent

Procedure

A suspension of 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.3 g), 3-aminopiperidine hydrochloride (0.905 g), triethylamine (3.0 g) in acetonitrile (40 ml) was refluxed for 5 hours and the reaction mixture was then cooled to room temperature. Removal of the solvent followed by purification by silica gel column chromatography (chloroform:methanol:ammonium hydroxide=15:5:1) gave a yellow crystalline substance [MS m/e: 378 (M+)]. The crystalline substance thus obtainedwas suspended in isopropanol and the suspension was adjusted to pH about 1-2 with 10% aqueous hydrochloric acid. Filtration of the precipitated crystals followed by recrystallization from ethanol afforded hydro-chloride of 5-amino-7-(3-aminopiperidin-1-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.6 g). m.p. 265° C. (decomposition).

Workup

  1. temperaturewas refluxed for 5 hours
  2. customRemoval of the solvent
  3. customfollowed by purification by silica gel column chromatography (chloroform:methanol:ammonium hydroxide=15:5:1)
  4. customgave a yellow crystalline substance [MS m/e: 378 (M+)]
  5. filtrationFiltration of the precipitated crystals
  6. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-58865a7211574e6780d4b4a26eaeb42e
Source dataset
uspto-grants-1991_09
Patent number
US05051509

Reaction notes

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