Trifluoroacetic acid → HCID 59398085, compound

HRID 2193305Notes

Reaction equation

HRID 2193305 reaction equation
C(OC(=O)[N:7]([CH2:33][C:34]1[CH:43]=[CH:42][C:37]2[O:38][CH2:39][CH2:40][O:41][C:36]=2[CH:35]=1)[CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]2[C:25]3[C:20](=[C:21]([O:26][CH2:27][C:28]([NH:30][CH3:31])=[O:29])[CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][C:17]2=[O:32])[CH2:10][CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[O:38]1[C:37]2[CH:42]=[CH:43][C:34]([CH2:33][NH:7][CH:8]3[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][N:16]4[C:25]5[C:20](=[C:21]([O:26][CH2:27][C:28]([NH:30][CH3:31])=[O:29])[CH:22]=[CH:23][CH:24]=5)[CH:19]=[CH:18][C:17]4=[O:32])[CH2:12][CH2:13]3)=[CH:35][C:36]=2[O:41][CH2:40][CH2:39]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59398123HCID 59398123, compound

Product 1

HCID 59398085HCID 59398085, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 2 mL of a chloroform solution containing 87 mg of tert-butyl(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(5-((methylamino)carbonylmethyloxy)-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 2 mL of trifluoroacetic acid was added and stirred at room temperature for 1 hour. After solvents of the reaction mixture were removed under reduced pressure and the residue was alkalized by aqueous saturated sodium hydrogen carbonate solution, it was extracted with ethyl acetate. The organic layer was washed sequentially with water and aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give 49 mg of (1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-2-oxo-1,2-dihydroquinolin-5-yloxy)-N-methylacetamide as a pale yellow foam.

Workup

  1. additionwas added
  2. customAfter solvents of the reaction mixture were removed under reduced pressure
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed sequentially with water and aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-24c940ce325b4b3ea8b3d3269e84ff05
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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