Triethylamine → HCID 14774109, compound

HRID 1081428Notes

Reaction equation

HRID 1081428 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[C:8]([CH3:16])[C:9]([F:15])=[C:10](F)[C:11]=2[F:13])[C:6](=[O:17])[C:5]([C:18]([OH:20])=[O:19])=[CH:4]1)[CH3:2].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:10]2[C:11]([F:13])=[C:12]3[C:7]([C:6](=[O:17])[C:5]([C:18]([OH:20])=[O:19])=[CH:4][N:3]3[CH2:1][CH3:2])=[C:8]([CH3:16])[C:9]=2[F:15])[CH2:30]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 14651268HCID 14651268, compound

Product 1

HCID 14774109HCID 14774109, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.36 g (1.25 mmol) of 1-ethyl-6,7,8-trifluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid, 0.26 g (1.39 mmol) of 3-(t-butoxycarbonyl) aminopyrrolidine, 0.38 g (3.76 mmol) of triethylamine, and 20 mL of acetonitrile was refluxed for 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 5 mL of 6N hydrochloric acid and 5 mL of glacial acetic acid and stirred for 5 hours at room temperature. The solution was concentrated to a solid which was suspended in water, made basic (pH 12), filtered through a fiberglass pad, and neutralized (pH 6.8). The solids were collected by filtration, washed with water, and dried in vacuo to give 0.32 g of white solid, mp 218°-220° C.

Workup

  1. temperaturewas refluxed for 5 hours
  2. filtrationThe solids were collected by filtration
  3. washwashed with acetonitrile and ether
  4. dissolutionThe crude product was dissolved in 5 mL of 6N hydrochloric acid
  5. stirring5 mL of glacial acetic acid and stirred for 5 hours at room temperature
  6. concentrationThe solution was concentrated to a solid which
  7. filtrationfiltered through a fiberglass pad, and neutralized (pH 6.8)
  8. filtrationThe solids were collected by filtration
  9. washwashed with water
  10. customdried in vacuo

Sources & evidence

ORD record
ord-02a52fb47b4a46c08ed7e51881391407
Source dataset
uspto-grants-1996_12
Patent number
US05585491

Reaction notes

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