Trifluoroacetic acid → N-[6-Chloro-2-(1-piperazinyl)-5-quinolinyl]-cyclohexanepropanamide

HRID 2217897Notes

Reaction equation

HRID 2217897 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:23])[C:8]=2[NH:12][C:13](=[O:22])[CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[N:3]=1.[N:24]1(C(OC(C)(C)C)=O)[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(N(CC)CC)C.FC(F)(F)C(O)=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[NH3:3].[Cl:23][C:7]1[C:8]([NH:12][C:13](=[O:22])[CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)[CH:11]=[CH:10]2

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 86012849N-(2,6-Dichloro-5-quinolinyl)-cyclohexanepropanamide

Product 2

HCID 222AmmoniaYield 10%HCID 11338570N-[6-Chloro-2-(1-piperazinyl)-5-quinolinyl]-cyclohexanepropanamideYield 32.9%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

N-(2,6-Dichloro-5-quinolinyl)-cyclohexanepropanamide (Example 90(a)) (0.16 g), 1-piperazinecarboxylic acid, 1,1-dimethylethyl ester (0.34 g,), triethylamine (0.15 mL) and tetra-butylammonium bromide (80 mg) were heated at 140° C. for 1 hour in a microwave. The resulting precipitate was filtered and then washed with acetonitrile to give a solid. This solid was dissolved in dichloromethane and trifluoroacetic acid (1 mL) was added. The reaction mixture was stirred at room temperature for 3 hours, then concentrated under vacuum to dryness. Purification (HPLC, Symmetry—0.1% aqueous trifluoroacetic acid:acetonitrile followed by Varian SCX cartridge using methanol and then 10% ammonia in methanol as eluant) gave the title compound as a white solid (30 mg).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with acetonitrile
  3. customto give a solid
  4. concentrationconcentrated under vacuum to dryness
  5. customPurification (HPLC, Symmetry—0.1% aqueous trifluoroacetic acid

Sources & evidence

ORD record
ord-9539e8fc7cbf472e9b7fb166b9aa4983
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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