1-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 15670693, compound

HRID 729070Notes

Reaction equation

HRID 729070 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[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.[C:21]([NH:24][CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][NH:28][CH2:27]1)(=[O:23])[CH3:22]>C(N(CC)CC)C>[C:21]([NH:24][CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][N:28]([C:11]2[C:12]([F:14])=[C:13]3[C:8]([C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5][N:4]3[CH:1]3[CH2:3][CH2:2]3)=[CH:9][C:10]=2[F:16])[CH2:27]1)(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 4712037N-(piperidin-3-ylmethyl)acetamide

Product 1

HCID 15670693HCID 15670693, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid(2.83 g), 3-acetamidomethylpiperidine (1.87 g) and triethylamine (1.5 g) inacetonitrile (60 ml) was refluxed with stirring for 6 hours. The precipitate was filtered to give 7-(3-acetamidomethylpiperidin-1-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (3.5 g). The product (3.0 g) was suspended in 6N hydrochloric acid (50 ml) and heated at 100° C. with stirring for 5 hours. The reaction mixture was concentrated in vacuum, and the crude material was dissolved in 20 ml of aqueous ammonium hydroxide under ice-cooling. Removal of the solvent followed by purification by silica gel column chromatography (chloroform:methanol:ammonium hydroxide=15:5:1) gave 7-(3-aminomethylpiperidin-1-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.6 g), which was recrystallized from methanol-water to afford colorless prisms. m.p. 242°-243° C.

Workup

  1. temperaturewas refluxed
  2. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-035c405b74e64c00839b9d577eac5dbd
Source dataset
uspto-grants-1991_09
Patent number
US05051509

Reaction notes

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