Trifluoroacetic acid → HCID 22648056, compound

HRID 394148Notes

Reaction equation

HRID 394148 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:17]=[C:16]([CH:18]2[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]2)[CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][C:12](=[O:39])[N:13]2[C:31]1[C:36]([Cl:37])=[CH:35][CH:34]=[CH:33][C:32]=1[Cl:38].FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:17]=[C:16]([CH:18]2[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]2)[CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][C:12](=[O:39])[N:13]2[C:31]1[C:32]([Cl:38])=[CH:33][CH:34]=[CH:35][C:36]=1[Cl:37]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22648002HCID 22648002, compound

Product 1

HCID 22648056HCID 22648056, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 50 mg of tert-butyl 4-[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl]piperidine-1-carboxylate in 5 mL of CH2Cl2 was added 2 mL of trifluoroacetic acid. The mixture was stirred at rt for 1 h, then concentrated. The residue was dissolved in 10 mL of CH2Cl2, washed with 5 mL NaHCO3, dried (Na2SO4), and concentrated. The residue was purified by preparative thin-layer chromatography, eluting with 95:5 CH2Cl2-2M NH3 in MeOH, followed by preparative HPLC (YMC C18 20×50 mm column; 10:90 to 100:0 v/v acetonitrile/water+0.1% TFA over 5 min; 20 mL/min) to yield the title compound.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in 10 mL of CH2Cl2
  3. washwashed with 5 mL NaHCO3
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by preparative thin-layer chromatography
  7. washeluting with 95:5 CH2Cl2-2M NH3 in MeOH
  8. customfollowed by preparative HPLC (YMC C18 20×50 mm column; 10:90 to 100:0 v/v acetonitrile/water+0.1% TFA over 5 min; 20 mL/min)

Sources & evidence

ORD record
ord-8ef4a77f007542068397341f9d8161bd
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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