Triethylamine → HCID 14774109, compound

HRID 2073851Notes

Reaction equation

HRID 2073851 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 five hours, then stirred at room temperature overnight. The solids were filtered 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 five 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 filtered and washed with water to give 0.32 g of white solid, mp 218°-220° C.

Workup

  1. temperaturewas refluxed for five hours
  2. filtrationThe solids were filtered
  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 five 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 filtered
  9. washwashed with water

Sources & evidence

ORD record
ord-3f496d6fb7524325ad63dd4cef046642
Source dataset
uspto-grants-1990_04
Patent number
US04920120

Reaction notes

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