Trifluoroacetic acid → 7-Chloro-4-(1-piperazinyl)-2-quinolinamine

HRID 1353440Notes

Reaction equation

HRID 1353440 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:20]3[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]3)=[CH:7][C:8]([NH:12]C(OC(C)(C)C)=O)=[N:9]2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)=[CH:7][C:8]([NH2:12])=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21101824HCID 21101824, compound

Product 1

HCID 211017487-Chloro-4-(1-piperazinyl)-2-quinolinamineYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred sloution of 4-[7-chloro-2-[[(1,1-dimethylethoxy)carbonyl]amino]-4-quinolinyl]-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester (2 g, 4.33 mmol) in CH2Cl2 (30 mL) was added TFA (4 mL) at rt. The reaction mixture was kept at reflux for 4 h, then cooled to rt. After removal of the solvent and excess TFA, the mixture was diluted with CH2Cl2, and treated with NaOH (10%) to pH 12. The mixture was extracted with CH2Cl2, washed with brine, and dried over Na2SO4. Concentration in vacuo afforded the product as a free base (1.13 g, 98%). LC-MS: 262 (M++1). 1H NMR (DMSO-d6): 62.90 (s, 8H), 6.20 (s, 1H), 6.4 (s, 2H) 7.08 (d, 1H), 7.35 (s, 1H), 7.68 (d, 1H).

Workup

  1. temperatureat reflux for 4 h
  2. customAfter removal of the solvent and excess TFA
  3. additionthe mixture was diluted with CH2Cl2
  4. additiontreated with NaOH (10%) to pH 12
  5. extractionThe mixture was extracted with CH2Cl2
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-cab2ddfdea734c8f854b0da43108bf02
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

Loading…