Trifluoroacetic acid → HCID 21101815, compound

HRID 1353327Notes

Reaction equation

HRID 1353327 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]([Cl:24])=[CH:21][CH:22]=3)[N:17]=[C:16]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+].[F:39][C:40]1[CH:45]=[CH:44][C:43]([N:46]=C=O)=[CH:42][CH:41]=1>C(Cl)Cl>[Cl:24][C:20]1[CH:19]=[C:18]2[C:23]([C:14]([N:11]3[CH2:10][CH2:9][N:8]([C:6]([NH:46][C:43]4[CH:44]=[CH:45][C:40]([F:39])=[CH:41][CH:42]=4)=[O:7])[CH2:13][CH2:12]3)=[CH:15][C:16]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[N:17]2)=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 709554-Fluorophenyl isocyanateHCID 21101814HCID 21101814, compound

Product 1

HCID 21101815HCID 21101815, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 4-[4-(tert-butoxycarbonyl)piperazin-1-yl]-7-chloroquinoline-2-carboxylate (1.0 g, 2.4 mmol) in CH2Cl2 (5 mL) is added trifluoroacetic acid (5 mL). After 1 h at room temp., the reaction mixture is adjusted to pH 10–11 with 10% aq. NaOH and extracted with EtOAc. The combined extracts are dried (Na2SO4) and concentrated. The residue is dissolved in CH2Cl2 (70 mL) and treated with 4-fluorophenyl isocyanate (0.32 mL, 2.8 mmol) for 15 h at room temp. The reaction mixture is washed with water and brine, dried (Na2SO4), and concentrated. The residue is purified by column chromatography with CH2Cl2-MeOH yielding the title product.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined extracts are dried (Na2SO4)
  3. concentrationconcentrated
  4. dissolutionThe residue is dissolved in CH2Cl2 (70 mL)
  5. washThe reaction mixture is washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue is purified by column chromatography with CH2Cl2-MeOH yielding the title product

Sources & evidence

ORD record
ord-cc8c6db846af45e5adeb3504a559f032
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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