Trifluoroacetic acid → HCID 71556553, compound

HRID 1497115Notes

Reaction equation

HRID 1497115 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]([CH:14]([CH3:16])[CH3:15])[CH3:13])[C:6]([C:17]([O:19]C(C)(C)C)=[O:18])=[C:5]2[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]([CH:14]([CH3:15])[CH3:16])[CH3:13])[C:6]([C:17]([OH:19])=[O:18])=[C:5]2[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86682966HCID 86682966, compound

Product 1

HCID 71556553HCID 71556553, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 6-chloro-2-(isopropyl(methyl)amino)-4-phenylquinoline-3-carboxylate (75 mg, 183 μmol), in DCM (1 ml) and TFA (1 ml) was stirred at room temperature for 2 h followed by a further 2 h at 40° C. The reaction mixture was concentrated in vacuo and the crude residue was dissolved in ethyl actetate and washed with water. The ethyl acetate layer was washed with 0.1N NaOH solution (2×) and then the aqueous layer was made acidic (pH 3-4) with 1N HCl and then further extracted with ethyl acetate. The organic layers were combined, dried over Na2SO4, filtered and concentrated in vacuo to give the desired product as a light yellow solid (48 mg, 74%). MS (ESI): 355 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe crude residue was dissolved in ethyl actetate
  3. washwashed with water
  4. washThe ethyl acetate layer was washed with 0.1N NaOH solution (2×)
  5. extractionfurther extracted with ethyl acetate
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1d0437f72d7f4f899a49bc018d9636fe
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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