Trifluoroacetic acid → 4-[4-(4-Fluorophenylaminocarbonyl)piperazin-1-yl]-7-nitroquinolin trifluoroacetate

HRID 1353323Notes

Reaction equation

HRID 1353323 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]3[C:18](=[CH:19][C:20]([N+:24]([O-:26])=[O:25])=[CH:21][CH:22]=3)[N:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])(C)(C)C.[F:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30].C(N(CC)CC)C.[F:41][C:42]1[CH:47]=[CH:46][C:45]([N:48]=C=O)=[CH:44][CH:43]=1>C(Cl)Cl>[F:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30].[F:41][C:42]1[CH:47]=[CH:46][C:45]([NH:48][C:6]([N:8]2[CH2:9][CH2:10][N:11]([C:14]3[C:23]4[C:18](=[CH:19][C:20]([N+:24]([O-:26])=[O:25])=[CH:21][CH:22]=4)[N:17]=[CH:16][CH:15]=3)[CH2:12][CH2:13]2)=[O:7])=[CH:44][CH:43]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 709554-Fluorophenyl isocyanateHCID 211017074-[4-(tert-Butoxycarbonyl)piperazin-1-yl]-7-nitroquinoline

Product 1

HCID 211016944-[4-(4-Fluorophenylaminocarbonyl)piperazin-1-yl]-7-nitroquinolin trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[4-(tert-butoxycarbonyl)piperazin-1-yl]-7-nitroquinoline (360 mg, 1 mmol) in CH2Cl2 (1 mL) is added trifluoroacetic acid (1 mL). After 1½ h at room temp., the mixture is concentrated, and the residue is dissolved in CH2Cl2 (20 mL) and treated with triethylamine (0.56 mL, 4 mmol) and 4-fluorophenyl isocyanate (0.16 mL, 1.4 mmol). After 1½ h stirring at room temp., the reaction mixture is washed with water and brine, dried (Na2SO4), and concentrated. The residue is purified by reversed phase HPLC with water-MeCN-TFA yielding the title product.

Workup

  1. waitAfter 1½ h at room temp.
  2. concentrationthe mixture is concentrated
  3. dissolutionthe residue is dissolved in CH2Cl2 (20 mL)
  4. washthe reaction mixture is washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue is purified by reversed phase HPLC with water-MeCN-TFA yielding the title product

Sources & evidence

ORD record
ord-d98e7f77fedf4aa580cf6406f9588ebf
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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