Trifluoroacetic acid → Ethyl (1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-2-oxo-1,2-dihydroquinolin-5-yloxy)acetate

HRID 2193272Notes

Reaction equation

HRID 2193272 reaction equation
C(OC([N:8]([CH2:35][C:36]1[CH:45]=[CH:44][C:39]2[O:40][CH2:41][CH2:42][O:43][C:38]=2[CH:37]=1)[CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]2[C:26]3[C:21](=[C:22]([O:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][C:18]2=[O:34])[CH2:11][CH2:10]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[O:40]1[C:39]2[CH:44]=[CH:45][C:36]([CH2:35][NH:8][CH:9]3[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][N:17]4[C:26]5[C:21](=[C:22]([O:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:23]=[CH:24][CH:25]=5)[CH:20]=[CH:19][C:18]4=[O:34])[CH2:13][CH2:14]3)=[CH:37][C:38]=2[O:43][CH2:42][CH2:41]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59398057HCID 59398057, compound

Product 1

HCID 59398317Ethyl (1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-2-oxo-1,2-dihydroquinolin-5-yloxy)acetateYield 68.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 2 mL of a chloroform solution containing 83 mg of ethyl (1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-2-oxo-1,2-dihydroquinolin-5-yloxy)acetate, 2 mL of trifluoroacetic acid was added and stirred at room temperature for 6 hours. After the solvent was 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 48 mg of ethyl (1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-2-oxo-1,2-dihydroquinolin-5-yloxy)acetate as a white solid.

Workup

  1. additionwas added
  2. customAfter the solvent was 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-27309596fee54d6684f0c0f2aa59d335
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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