Triethylamine → HCID 14651214, compound

HRID 1081427Notes

Reaction equation

HRID 1081427 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 4 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 4 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 7.1), and the precipitate was collected by filtration, washed with water, and dried in vacuo to give 0.29 g of the title compound, mp 124°-126° C.

Workup

  1. temperaturewas refluxed for 4 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 4 hours
  7. concentrationThe solution was concentrated to a gold solid which
  8. filtrationfiltered
  9. filtrationthe precipitate was collected by filtration
  10. washwashed with water
  11. customdried in vacuo

Sources & evidence

ORD record
ord-7acaee00a0c749f28acba909f817dcd1
Source dataset
uspto-grants-1996_12
Patent number
US05585491

Reaction notes

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