Triethylamine → 7-(3-Amino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid

HRID 1081424Notes

Reaction equation

HRID 1081424 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:16])[C:10]([F:15])=[C:11](F)[CH:12]=3)[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.C(OC([NH:28][CH:29]1[CH2:33][CH2:32][NH:31][CH2:30]1)=O)(C)(C)C.C(N(CC)CC)C>C(#N)C>[NH2:28][CH:29]1[CH2:33][CH2:32][N:31]([C:11]2[CH:12]=[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)=[C:9]([CH3:16])[C:10]=2[F:15])[CH2:30]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 146512541-Cyclopropyl-6,7-difluoro-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 146511687-(3-Amino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acidYield 110%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.70 g (2.50 mmol) of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid, 0.56 g (3.00 mmol) of 3-(t-butoxycarbonyl) aminopyrrolidine, 0.76 g (7.52 mmol) of triethylamine, and 25 mL of acetonitrile was refluxed for 4.5 hours, then stirred at room temperature overnight. The solids were collected by filtration and washed with acetonitrile and ether. The crude product was dissolved in 20 mL of 6N hydrochloric acid and 20 mL of acetic acid and was stirred at room temperature for 3 hours. The solution was concentrated to an oil which was triturated with 2:1 ether:isopropanol. The solids were removed by filtration, washed with ether, and dried to give 0.95 g of the title compound as the hydrochloride salt, mp>300° C.

Workup

  1. temperaturewas refluxed for 4.5 hours
  2. filtrationThe solids were collected by filtration
  3. washwashed with acetonitrile and ether
  4. dissolutionThe crude product was dissolved in 20 mL of 6N hydrochloric acid
  5. stirring20 mL of acetic acid and was stirred at room temperature for 3 hours
  6. concentrationThe solution was concentrated to an oil which
  7. customwas triturated with 2:1 ether
  8. customThe solids were removed by filtration
  9. washwashed with ether
  10. customdried

Sources & evidence

ORD record
ord-ee961508d7d64b319e01592b325fa407
Source dataset
uspto-grants-1996_12
Patent number
US05585491

Reaction notes

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