Trifluoroacetic acid → HCID 178507808, compound

HRID 2290029Notes

Reaction equation

HRID 2290029 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([F:18])[CH:17]=1)[N:14]=[CH:13][C:12]([C:19]([NH:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)=[O:20])=[C:11]2[OH:30])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([F:18])[CH:17]=1)[N:14]=[CH:13][C:12]([C:19]([NH:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)=[O:20])=[C:11]2[OH:30]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178452814HCID 178452814, compound

Product 1

HCID 178507808HCID 178507808, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a flask containing tert-butyl-3-{[(4-chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-quinolinylcarbamate from Preparation No. 25 (0.06 g) and dichloromethane (2 mL) is added trifluoroacetic acid (2 mL). The reaction mixture is stirred 1 hour then concentrated under reduced pressure. The residue is triturated with toluene (3×) and dried in vacuo. The residue is adsorbed onto silica and chromatographed on silica eluting with 2% MeOH:CH2Cl2 to 6% MeOH:CH2Cl2. The product-containing fractions are evaporated to give 0.04 g of the title compound as a tan solid.

Workup

  1. customfrom Preparation No
  2. concentrationthen concentrated under reduced pressure
  3. customThe residue is triturated with toluene (3×)
  4. customdried in vacuo
  5. customchromatographed on silica eluting with 2% MeOH
  6. customThe product-containing fractions are evaporated

Sources & evidence

ORD record
ord-217592d1e21f42c093b20c86c1112fcf
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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