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

HRID 2073846Notes

Reaction equation

HRID 2073846 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 filtered 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 three hours. The solution was concentrated to an oil which was triturated with 2:1 ether:isopropanol. The solids were filtered and washed with ether 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 filtered
  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 three hours
  6. concentrationThe solution was concentrated to an oil which
  7. customwas triturated with 2:1 ether
  8. filtrationThe solids were filtered
  9. washwashed with ether

Sources & evidence

ORD record
ord-c2adcd252f944b80b9e0c76534ecb1e6
Source dataset
uspto-grants-1990_04
Patent number
US04920120

Reaction notes

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