Trifluoroacetic acid → HCID 20817831, compound

HRID 897219Notes

Reaction equation

HRID 897219 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([Cl:25])[CH:23]=3)[N:18]([CH2:26][C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)[C:17](=[O:33])[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.BrC[C:43]1[CH:52]=[CH:51][C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]=1>C(Cl)Cl.C(OCC)(=O)C>[Cl:25][C:22]1[CH:21]=[C:20]2[C:19](=[CH:24][CH:23]=1)[N:18]([CH2:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1)[C:17](=[O:33])[CH:16]=[C:15]2[NH:14][CH:11]1[CH2:10][CH2:9][N:8]([CH2:6][C:43]2[CH:52]=[CH:51][C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[CH:44]=2)[CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 703202-BromomethylnaphthaleneHCID 69738349HCID 69738349, compound

Product 1

HCID 20817831HCID 20817831, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(6-Chloro-2-oxo-1-pyridin-4-ylmethyl-1,2-dihydroquinolin-4-ylamino)-piperidine-1-carboxylic acid t-butyl ester (0.58 g, 1.2 mmol) was dissolved in DCM (10 mL) and treated with trifluoroacetic acid (5 mL). The solution was stirred for 15 minutes before evaporating under reduced pressure. The crude amine was dissolved in acetonitrile (25 mL) prior to addition of sodium carbonate (1.22 g) and a drop of triethylamine. The mixture was stirred for 5 minutes before addition of 2-(bromomethyl)naphthalene (0.31 g, 1.4 mmol). After 2 hours the reaction was found to be complete by TLC analysis and the mixture was diluted with ethyl acetate, washed with 1N NaOH, and dried with sodium sulfate. Evaporation under reduced pressure gave the crude product which was purified by silica chromatography using DCM and methanol eluent to give the title compound (0.42 g). 1H NMR (300 MHz, CDCl3) δ ppm 2.04 (2H, m), 2.22 (2H, m), 2.67 (2H, m), 3.23 (2H, m), 3.67 (1H, m), 4.02 (2H, s), 5.20 (1H, m), 5.47 (2H, m), 5.82 (1H, s), 6.93 (1H, d, J=8.96 Hz), 7.05 (2H, m), 7.32 (1H, m), 7.46-7.52 (2H, m), 7.65 (1H, m), 7.72 (1H, m), 7.84 (3H, m), 7.91 (1H, m), 8.48 (2H, m).

Workup

  1. custombefore evaporating under reduced pressure
  2. dissolutionThe crude amine was dissolved in acetonitrile (25 mL)
  3. additionto addition of sodium carbonate (1.22 g)
  4. waitAfter 2 hours the reaction was found
  5. washwashed with 1N NaOH
  6. dry with materialdried with sodium sulfate
  7. customEvaporation under reduced pressure
  8. customgave the crude product which
  9. customwas purified by silica chromatography

Sources & evidence

ORD record
ord-9441871b4ce241aca0c23ed1f488cb56
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

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