Triethylamine → HCID 14651214, compound

HRID 2073849Notes

Reaction equation

HRID 2073849 reaction equation
[Cl:1][C:2]1[C:3](F)=[C:4]([F:20])[C:5]([CH3:19])=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([OH:17])=[O:16])[C:7]2=[O:18].C(OC([NH:29][CH:30]1[CH2:34][CH2:33][NH:32][CH2:31]1)=O)(C)(C)C.C(N(CC)CC)C>C(#N)C>[NH2:29][CH:30]1[CH2:34][CH2:33][N:32]([C:3]2[C:2]([Cl:1])=[C:11]3[C:6]([C:7](=[O:18])[C:8]([C:15]([OH:17])=[O:16])=[CH:9][N:10]3[CH:12]3[CH2:14][CH2:13]3)=[C:5]([CH3:19])[C:4]=2[F:20])[CH2:31]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 14651260HCID 14651260, compound

Product 1

HCID 14651214HCID 14651214, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.50 g (1.60 mmol) of 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid, 0.36 g (1.93 mmol) of 3-(t-butoxycarbonyl)aminopyrrolidine, 0.48 g (4.75 mmol) of triethylamine, and 20 ml of acetonitrile was refluxed for four hours, then stirred at room temperature overnight. The solution was concentrated and the residue was triturated with ether:hexane (1:1) and filtered. The solid was washed with water and hexane. The crude product was suspended in 15 ml of dichloromethane and 1.5 ml of trifluoroacetic acid and was stirred at room temperature for four hours. The solution was concentrated to a gold solid which was suspended in water, made basic (pH 11) with 10% sodium hydroxide, and filtered. The solution was then neutralized (pH 7.10), and the precipitate was filtered and washed with water to give 0.29 g of the title compound, mp 124°-126° C.

Workup

  1. temperaturewas refluxed for four hours
  2. concentrationThe solution was concentrated
  3. customthe residue was triturated with ether:hexane (1:1)
  4. filtrationfiltered
  5. washThe solid was washed with water and hexane
  6. stirring1.5 ml of trifluoroacetic acid and was stirred at room temperature for four hours
  7. concentrationThe solution was concentrated to a gold solid which
  8. filtrationfiltered
  9. filtrationthe precipitate was filtered
  10. washwashed with water

Sources & evidence

ORD record
ord-9361141167254706b29c4cc36f74caa0
Source dataset
uspto-grants-1990_04
Patent number
US04920120

Reaction notes

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